(S)-(+)-Mandelic acid
Número de catálogo B119166
Peso molecular: 152.15 g/mol
Clave InChI: IWYDHOAUDWTVEP-UHFFFAOYSA-N
Atención: Solo para uso de investigación. No para uso humano o veterinario.
Patent
US04983771
Procedure details
To the filtrate remaining after process A above was added 201 grams of 50% sodium hydroxide solution, for a pH of 12.9. The basic solution was extracted 3 times with toluene, for a total toluene addition of 325 grams. The toluene and (-)PEA were distilled off under vacuum, resulting in a recovery of 303.6 grams (93.4%) of toluene, and L(-)PEA in about 260.2 grams. The sodium mandelate/sodium acetate phase was neutralized with 305.4 grams HCl, giving a pH of about 0.8. This was extracted 4 times with MIBK, in a fashion similar to that above, for a total addition of 295.3 grams MIBK. 185 grams H2O was added to the MIBK, and the MIBK was distilled off with azeotropic distillation, returning 274.4 grams or 92.9% MIBK recovery. The mandelic acid recovered from this process, together with that recovered above, gave a total recovery of 299.44 grams mandelic acid, or an 89.5% return.
Name
sodium mandelate sodium acetate
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Name
Identifiers
|
REACTION_CXSMILES
|
[OH-].[Na+].[C:3]([O-:13])(=[O:12])[CH:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[OH:5].[Na+].C([O-])(=O)C.[Na+].Cl>>[C:3]([OH:13])(=[O:12])[CH:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[OH:5] |f:0.1,2.3.4.5|
|
Inputs
Step One
|
Name
|
|
|
Quantity
|
201 g
|
|
Type
|
reactant
|
|
Smiles
|
[OH-].[Na+]
|
Step Two
|
Name
|
sodium mandelate sodium acetate
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
C(C(O)C1=CC=CC=C1)(=O)[O-].[Na+].C(C)(=O)[O-].[Na+]
|
Step Three
|
Name
|
|
|
Quantity
|
305.4 g
|
|
Type
|
reactant
|
|
Smiles
|
Cl
|
Conditions
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
EXTRACTION
|
Type
|
EXTRACTION
|
|
Details
|
The basic solution was extracted 3 times with toluene
|
ADDITION
|
Type
|
ADDITION
|
|
Details
|
for a total toluene addition of 325 grams
|
DISTILLATION
|
Type
|
DISTILLATION
|
|
Details
|
The toluene and (-)PEA were distilled off under vacuum
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
resulting in a recovery of 303.6 grams (93.4%) of toluene, and L(-)PEA in about 260.2 grams
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
giving a pH of about 0.8
|
EXTRACTION
|
Type
|
EXTRACTION
|
|
Details
|
This was extracted 4 times with MIBK
|
ADDITION
|
Type
|
ADDITION
|
|
Details
|
in a fashion similar to that above, for a total addition of 295.3 grams MIBK
|
ADDITION
|
Type
|
ADDITION
|
|
Details
|
185 grams H2O was added to the MIBK
|
DISTILLATION
|
Type
|
DISTILLATION
|
|
Details
|
the MIBK was distilled off with azeotropic distillation
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
The mandelic acid recovered from this process
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
together with that recovered above,
|
Outcomes
Product
|
Name
|
|
|
Type
|
product
|
|
Smiles
|
C(C(O)C1=CC=CC=C1)(=O)O
|
Measurements
| Type | Value | Analysis |
|---|---|---|
| AMOUNT: MASS | 299.44 g |
Source
|
Source
|
Open Reaction Database (ORD) |
|
Description
|
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks. |
Patent
US04983771
Procedure details
To the filtrate remaining after process A above was added 201 grams of 50% sodium hydroxide solution, for a pH of 12.9. The basic solution was extracted 3 times with toluene, for a total toluene addition of 325 grams. The toluene and (-)PEA were distilled off under vacuum, resulting in a recovery of 303.6 grams (93.4%) of toluene, and L(-)PEA in about 260.2 grams. The sodium mandelate/sodium acetate phase was neutralized with 305.4 grams HCl, giving a pH of about 0.8. This was extracted 4 times with MIBK, in a fashion similar to that above, for a total addition of 295.3 grams MIBK. 185 grams H2O was added to the MIBK, and the MIBK was distilled off with azeotropic distillation, returning 274.4 grams or 92.9% MIBK recovery. The mandelic acid recovered from this process, together with that recovered above, gave a total recovery of 299.44 grams mandelic acid, or an 89.5% return.
Name
sodium mandelate sodium acetate
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Name
Identifiers
|
REACTION_CXSMILES
|
[OH-].[Na+].[C:3]([O-:13])(=[O:12])[CH:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[OH:5].[Na+].C([O-])(=O)C.[Na+].Cl>>[C:3]([OH:13])(=[O:12])[CH:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[OH:5] |f:0.1,2.3.4.5|
|
Inputs
Step One
|
Name
|
|
|
Quantity
|
201 g
|
|
Type
|
reactant
|
|
Smiles
|
[OH-].[Na+]
|
Step Two
|
Name
|
sodium mandelate sodium acetate
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
C(C(O)C1=CC=CC=C1)(=O)[O-].[Na+].C(C)(=O)[O-].[Na+]
|
Step Three
|
Name
|
|
|
Quantity
|
305.4 g
|
|
Type
|
reactant
|
|
Smiles
|
Cl
|
Conditions
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
EXTRACTION
|
Type
|
EXTRACTION
|
|
Details
|
The basic solution was extracted 3 times with toluene
|
ADDITION
|
Type
|
ADDITION
|
|
Details
|
for a total toluene addition of 325 grams
|
DISTILLATION
|
Type
|
DISTILLATION
|
|
Details
|
The toluene and (-)PEA were distilled off under vacuum
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
resulting in a recovery of 303.6 grams (93.4%) of toluene, and L(-)PEA in about 260.2 grams
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
giving a pH of about 0.8
|
EXTRACTION
|
Type
|
EXTRACTION
|
|
Details
|
This was extracted 4 times with MIBK
|
ADDITION
|
Type
|
ADDITION
|
|
Details
|
in a fashion similar to that above, for a total addition of 295.3 grams MIBK
|
ADDITION
|
Type
|
ADDITION
|
|
Details
|
185 grams H2O was added to the MIBK
|
DISTILLATION
|
Type
|
DISTILLATION
|
|
Details
|
the MIBK was distilled off with azeotropic distillation
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
The mandelic acid recovered from this process
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
together with that recovered above,
|
Outcomes
Product
|
Name
|
|
|
Type
|
product
|
|
Smiles
|
C(C(O)C1=CC=CC=C1)(=O)O
|
Measurements
| Type | Value | Analysis |
|---|---|---|
| AMOUNT: MASS | 299.44 g |
Source
|
Source
|
Open Reaction Database (ORD) |
|
Description
|
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks. |
Patent
US04983771
Procedure details
To the filtrate remaining after process A above was added 201 grams of 50% sodium hydroxide solution, for a pH of 12.9. The basic solution was extracted 3 times with toluene, for a total toluene addition of 325 grams. The toluene and (-)PEA were distilled off under vacuum, resulting in a recovery of 303.6 grams (93.4%) of toluene, and L(-)PEA in about 260.2 grams. The sodium mandelate/sodium acetate phase was neutralized with 305.4 grams HCl, giving a pH of about 0.8. This was extracted 4 times with MIBK, in a fashion similar to that above, for a total addition of 295.3 grams MIBK. 185 grams H2O was added to the MIBK, and the MIBK was distilled off with azeotropic distillation, returning 274.4 grams or 92.9% MIBK recovery. The mandelic acid recovered from this process, together with that recovered above, gave a total recovery of 299.44 grams mandelic acid, or an 89.5% return.
Name
sodium mandelate sodium acetate
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Name
Identifiers
|
REACTION_CXSMILES
|
[OH-].[Na+].[C:3]([O-:13])(=[O:12])[CH:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[OH:5].[Na+].C([O-])(=O)C.[Na+].Cl>>[C:3]([OH:13])(=[O:12])[CH:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[OH:5] |f:0.1,2.3.4.5|
|
Inputs
Step One
|
Name
|
|
|
Quantity
|
201 g
|
|
Type
|
reactant
|
|
Smiles
|
[OH-].[Na+]
|
Step Two
|
Name
|
sodium mandelate sodium acetate
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
C(C(O)C1=CC=CC=C1)(=O)[O-].[Na+].C(C)(=O)[O-].[Na+]
|
Step Three
|
Name
|
|
|
Quantity
|
305.4 g
|
|
Type
|
reactant
|
|
Smiles
|
Cl
|
Conditions
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
EXTRACTION
|
Type
|
EXTRACTION
|
|
Details
|
The basic solution was extracted 3 times with toluene
|
ADDITION
|
Type
|
ADDITION
|
|
Details
|
for a total toluene addition of 325 grams
|
DISTILLATION
|
Type
|
DISTILLATION
|
|
Details
|
The toluene and (-)PEA were distilled off under vacuum
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
resulting in a recovery of 303.6 grams (93.4%) of toluene, and L(-)PEA in about 260.2 grams
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
giving a pH of about 0.8
|
EXTRACTION
|
Type
|
EXTRACTION
|
|
Details
|
This was extracted 4 times with MIBK
|
ADDITION
|
Type
|
ADDITION
|
|
Details
|
in a fashion similar to that above, for a total addition of 295.3 grams MIBK
|
ADDITION
|
Type
|
ADDITION
|
|
Details
|
185 grams H2O was added to the MIBK
|
DISTILLATION
|
Type
|
DISTILLATION
|
|
Details
|
the MIBK was distilled off with azeotropic distillation
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
The mandelic acid recovered from this process
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
together with that recovered above,
|
Outcomes
Product
|
Name
|
|
|
Type
|
product
|
|
Smiles
|
C(C(O)C1=CC=CC=C1)(=O)O
|
Measurements
| Type | Value | Analysis |
|---|---|---|
| AMOUNT: MASS | 299.44 g |
Source
|
Source
|
Open Reaction Database (ORD) |
|
Description
|
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks. |
