(S)-(+)-Mandelic acid
货号 B119166
分子量: 152.15 g/mol
InChI 键: IWYDHOAUDWTVEP-UHFFFAOYSA-N
注意: 仅供研究使用。不适用于人类或兽医用途。
Patent
US04259521
Procedure details
To a portion (1100 mls out of a total of 4800 mls) of the mother liquor plus methanol wash liquor obtained from resolution B, containing about 2.4 moles of a mixture of diastereomers, consisting of about 2.25 moles of (-)-2-amino-1-butanol L-(+)-mandelate and about 0.15 mole of (-)-2-amino-1-butanol D-(-)-mandelate, is added 180 grams of potassium hydroxide (88.8% real; 2.85 moles) to obtain a solution having an initial αD25°C. of +24.7° ("as is", 10 cm cell). The solution is then heated at 115°-116° C. under pressure (40 psi) for 4 hours to obtain a mandelic acid solution having an αD25°C. of -3.0° ("as is", 10 cm cell). The resulting solution is essentially racemized, the negative rotation being due to the presence of the (-)-2-amino-1-butanol.
[Compound]
Name
mixture
Quantity
2.4 mol
Type
reactant
Reaction Step One
Name
(-)-2-amino-1-butanol L-(+)-mandelate
Quantity
2.25 mol
Type
reactant
Reaction Step Two
Name
(-)-2-amino-1-butanol D-(-)-mandelate
Quantity
0.15 mol
Type
reactant
Reaction Step Three
Identifiers
|
REACTION_CXSMILES
|
[C:1]([O:11]CC(N)CC)(=[O:10])[C@H:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3].C(OCC(N)CC)(=O)[C@@H](C1C=CC=CC=1)O.[OH-].[K+]>>[C:1]([OH:11])(=[O:10])[CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3] |f:2.3|
|
Inputs
Step One
[Compound]
|
Name
|
mixture
|
|
Quantity
|
2.4 mol
|
|
Type
|
reactant
|
|
Smiles
|
|
Step Two
|
Name
|
(-)-2-amino-1-butanol L-(+)-mandelate
|
|
Quantity
|
2.25 mol
|
|
Type
|
reactant
|
|
Smiles
|
C([C@@H](O)C1=CC=CC=C1)(=O)OCC(CC)N
|
Step Three
|
Name
|
(-)-2-amino-1-butanol D-(-)-mandelate
|
|
Quantity
|
0.15 mol
|
|
Type
|
reactant
|
|
Smiles
|
C([C@H](O)C1=CC=CC=C1)(=O)OCC(CC)N
|
Step Four
|
Name
|
|
|
Quantity
|
180 g
|
|
Type
|
reactant
|
|
Smiles
|
[OH-].[K+]
|
Conditions
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
WASH
|
Type
|
WASH
|
|
Details
|
To a portion (1100 mls out of a total of 4800 mls) of the mother liquor plus methanol wash liquor
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
obtained from resolution B
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
to obtain a solution
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
αD25°C. of +24.7° ("as is", 10 cm cell)
|
TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
The solution is then heated at 115°-116° C. under pressure (40 psi) for 4 hours
|
|
Duration
|
4 h
|
Outcomes
Product
|
Name
|
|
|
Type
|
product
|
|
Smiles
|
C(C(O)C1=CC=CC=C1)(=O)O
|
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
US04259521
Procedure details
To a portion (1100 mls out of a total of 4800 mls) of the mother liquor plus methanol wash liquor obtained from resolution B, containing about 2.4 moles of a mixture of diastereomers, consisting of about 2.25 moles of (-)-2-amino-1-butanol L-(+)-mandelate and about 0.15 mole of (-)-2-amino-1-butanol D-(-)-mandelate, is added 180 grams of potassium hydroxide (88.8% real; 2.85 moles) to obtain a solution having an initial αD25°C. of +24.7° ("as is", 10 cm cell). The solution is then heated at 115°-116° C. under pressure (40 psi) for 4 hours to obtain a mandelic acid solution having an αD25°C. of -3.0° ("as is", 10 cm cell). The resulting solution is essentially racemized, the negative rotation being due to the presence of the (-)-2-amino-1-butanol.
[Compound]
Name
mixture
Quantity
2.4 mol
Type
reactant
Reaction Step One
Name
(-)-2-amino-1-butanol L-(+)-mandelate
Quantity
2.25 mol
Type
reactant
Reaction Step Two
Name
(-)-2-amino-1-butanol D-(-)-mandelate
Quantity
0.15 mol
Type
reactant
Reaction Step Three
Identifiers
|
REACTION_CXSMILES
|
[C:1]([O:11]CC(N)CC)(=[O:10])[C@H:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3].C(OCC(N)CC)(=O)[C@@H](C1C=CC=CC=1)O.[OH-].[K+]>>[C:1]([OH:11])(=[O:10])[CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3] |f:2.3|
|
Inputs
Step One
[Compound]
|
Name
|
mixture
|
|
Quantity
|
2.4 mol
|
|
Type
|
reactant
|
|
Smiles
|
|
Step Two
|
Name
|
(-)-2-amino-1-butanol L-(+)-mandelate
|
|
Quantity
|
2.25 mol
|
|
Type
|
reactant
|
|
Smiles
|
C([C@@H](O)C1=CC=CC=C1)(=O)OCC(CC)N
|
Step Three
|
Name
|
(-)-2-amino-1-butanol D-(-)-mandelate
|
|
Quantity
|
0.15 mol
|
|
Type
|
reactant
|
|
Smiles
|
C([C@H](O)C1=CC=CC=C1)(=O)OCC(CC)N
|
Step Four
|
Name
|
|
|
Quantity
|
180 g
|
|
Type
|
reactant
|
|
Smiles
|
[OH-].[K+]
|
Conditions
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
WASH
|
Type
|
WASH
|
|
Details
|
To a portion (1100 mls out of a total of 4800 mls) of the mother liquor plus methanol wash liquor
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
obtained from resolution B
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
to obtain a solution
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
αD25°C. of +24.7° ("as is", 10 cm cell)
|
TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
The solution is then heated at 115°-116° C. under pressure (40 psi) for 4 hours
|
|
Duration
|
4 h
|
Outcomes
Product
|
Name
|
|
|
Type
|
product
|
|
Smiles
|
C(C(O)C1=CC=CC=C1)(=O)O
|
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
US04259521
Procedure details
To a portion (1100 mls out of a total of 4800 mls) of the mother liquor plus methanol wash liquor obtained from resolution B, containing about 2.4 moles of a mixture of diastereomers, consisting of about 2.25 moles of (-)-2-amino-1-butanol L-(+)-mandelate and about 0.15 mole of (-)-2-amino-1-butanol D-(-)-mandelate, is added 180 grams of potassium hydroxide (88.8% real; 2.85 moles) to obtain a solution having an initial αD25°C. of +24.7° ("as is", 10 cm cell). The solution is then heated at 115°-116° C. under pressure (40 psi) for 4 hours to obtain a mandelic acid solution having an αD25°C. of -3.0° ("as is", 10 cm cell). The resulting solution is essentially racemized, the negative rotation being due to the presence of the (-)-2-amino-1-butanol.
[Compound]
Name
mixture
Quantity
2.4 mol
Type
reactant
Reaction Step One
Name
(-)-2-amino-1-butanol L-(+)-mandelate
Quantity
2.25 mol
Type
reactant
Reaction Step Two
Name
(-)-2-amino-1-butanol D-(-)-mandelate
Quantity
0.15 mol
Type
reactant
Reaction Step Three
Identifiers
|
REACTION_CXSMILES
|
[C:1]([O:11]CC(N)CC)(=[O:10])[C@H:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3].C(OCC(N)CC)(=O)[C@@H](C1C=CC=CC=1)O.[OH-].[K+]>>[C:1]([OH:11])(=[O:10])[CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3] |f:2.3|
|
Inputs
Step One
[Compound]
|
Name
|
mixture
|
|
Quantity
|
2.4 mol
|
|
Type
|
reactant
|
|
Smiles
|
|
Step Two
|
Name
|
(-)-2-amino-1-butanol L-(+)-mandelate
|
|
Quantity
|
2.25 mol
|
|
Type
|
reactant
|
|
Smiles
|
C([C@@H](O)C1=CC=CC=C1)(=O)OCC(CC)N
|
Step Three
|
Name
|
(-)-2-amino-1-butanol D-(-)-mandelate
|
|
Quantity
|
0.15 mol
|
|
Type
|
reactant
|
|
Smiles
|
C([C@H](O)C1=CC=CC=C1)(=O)OCC(CC)N
|
Step Four
|
Name
|
|
|
Quantity
|
180 g
|
|
Type
|
reactant
|
|
Smiles
|
[OH-].[K+]
|
Conditions
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
WASH
|
Type
|
WASH
|
|
Details
|
To a portion (1100 mls out of a total of 4800 mls) of the mother liquor plus methanol wash liquor
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
obtained from resolution B
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
to obtain a solution
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
αD25°C. of +24.7° ("as is", 10 cm cell)
|
TEMPERATURE
|
Type
|
TEMPERATURE
|
|
Details
|
The solution is then heated at 115°-116° C. under pressure (40 psi) for 4 hours
|
|
Duration
|
4 h
|
Outcomes
Product
|
Name
|
|
|
Type
|
product
|
|
Smiles
|
C(C(O)C1=CC=CC=C1)(=O)O
|
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. |
