Benzene → Mandelic Acid

HRID 1583719Notes

Reaction equation

HRID 1583719 reaction equation
C([OH:4])(C)C.[CH2:5]([OH:8])[CH2:6][CH3:7].[CH2:9]([OH:11])C.[CH:12]1C=C[CH:15]=[CH:14][CH:13]=1>C1(C)C=CC=CC=1>[C:9]([OH:11])(=[O:4])[CH:5]([C:6]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:7]=1)[OH:8]

Participants

6

Reactant 4

HCID 241BenzeneHCID 702EthanolHCID 10311-PropanolHCID 3776Isopropanol

Product 1

HCID 1292Mandelic Acid

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The hydrogenation reaction preferably takes place in the presence of a solvent which is inert to the reactants, for example, isopropyl alcohol, n-propyl alcohol, ethanol, benzene and toluene. At the end of the reaction, the reaction mass is filtered, stripped of solvent and distilled as by fractional distillation. If desired, the reaction product defined according to the structure: ##STR39## may be used as is for its organoleptic properties or it may be further purified by means of standard "d" and "l" separation, for example, by producing esters from optically active acids such as d or l mandelic acid, separating the resulting stereoisomers by means of fractional crystalization and then hydrolyzing the resulting esters back to the alcohols defined according to the structures:

Workup

  1. customThe hydrogenation reaction preferably takes place in the presence of a solvent which
  2. customAt the end of the reaction
  3. filtrationthe reaction mass is filtered
  4. distillationdistilled as by fractional distillation

Sources & evidence

ORD record
ord-50bac671ac5c48d9a3444b0aa07b61bb
Source dataset
uspto-grants-1985_11
Patent number
US04554096

Reaction notes

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