Glyoxylic Acid → (+-)-4-Hydroxymandelic acid
Reaction equation
[C:1]([OH:5])(=[O:4])[CH:2]=[O:3].[C:6]1([OH:12])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>O>[OH:12][C:6]1[CH:11]=[CH:10][C:9]([CH:2]([OH:3])[C:1]([OH:5])=[O:4])=[CH:8][CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
The European patent specification EP-0,368,696 describes the condensation of a glyoxylic acid with phenol in the presence of a water-insoluble amine, to form a 12:84 mixture of 2- and 4-hydroxymandelic acid respectively. Then the excess of phenol is extracted with 1,1-dimethyl-1-methoxypropane. Only 70-74% of the paraisomer, 4-hydroxymandelic acid, is isolated leaving a non-separable mixture of approximately 1:1 2- and 4-hydroxymandelic acid.
Workup
- customto form
- extractionThen the excess of phenol is extracted with 1,1-dimethyl-1-methoxypropane
Sources & evidence
- ORD record
- ord-89b113ed39194d25bd2436f24bca2c8a
- Source dataset
- uspto-grants-2002_03
- Patent number
- US06359172B1
Reaction notes
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