Formaldehyde → 2,3-Dihydroxy-1,2-diphenylpropan-1-one

HRID 1612899Notes

Reaction equation

HRID 1612899 reaction equation
[C:1]1([C:7]([CH:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[OH:10])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:17]=[O:18].[OH-].[K+]>CS(C)=O>[OH:18][CH2:17][C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([OH:10])[C:7](=[O:8])[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 8400BenzoinHCID 14797Potassium Hydroxide

Product 1

HCID 858062,3-Dihydroxy-1,2-diphenylpropan-1-oneYield 99%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A solution of 100 parts of benzoin in 240 parts of dimethyl sulfoxide was added dropwise over 10 minutes to a dispersion of 17 parts of paraformaldehyde having a purity of 75% and 2.6 parts of potassium hydroxide in 580 parts of dimethyl sulfoxide and the mixture was agitated for further 15 minutes to effect the reaction which was terminated with addition of diluted hydrochloric acid followed by the admixture of the reaction mixture with 900 parts of water. The thus obtained aqueous solution was extracted with ethyl acetate and the ethyl acetate extract was washed with a saturated aqueous solution of sodium chloride and concentrated by evaporating the solvent under reduced pressure to give 113 parts of α-hydroxymethyl benzoin. The yield was more than 99% of the theoretical value.

Workup

  1. customthe reaction which
  2. customwas terminated with addition of diluted hydrochloric acid
  3. extractionThe thus obtained aqueous solution was extracted with ethyl acetate
  4. extractionthe ethyl acetate extract
  5. washwas washed with a saturated aqueous solution of sodium chloride
  6. concentrationconcentrated
  7. customby evaporating the solvent under reduced pressure

Sources & evidence

ORD record
ord-0ab56893c4d34c749baf263e9a12f506
Source dataset
uspto-grants-1993_03
Patent number
US05190988

Reaction notes

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