Benzyl Alcohol → Methyl 3-benzyloxy-3-phenyl-2-hydroxybutyrate

HRID 1941105Notes

Reaction equation

HRID 1941105 reaction equation
[C:1]1([C:7]2([CH3:14])[O:13][CH:8]2[C:9]([O:11][CH3:12])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(=O)(=O)(O)O.[CH2:20]([OH:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[CH2:20]([O:27][C:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([CH3:14])[CH:8]([OH:13])[C:9]([O:11][CH3:12])=[O:10])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 3

HCID 244Benzyl AlcoholHCID 1118Sulfuric AcidHCID 228011Methyl 3-methyl-3-phenyloxirane-2-carboxylate

Product 1

HCID 15292268Methyl 3-benzyloxy-3-phenyl-2-hydroxybutyrate

Procedure

9.6 g (50 mmol) of methyl 3-phenyl-2,3-epoxybutyrate are dissolved in 150 ml of benzyl alcohol, and 0.5 ml of concentrated sulfuric acid is added. Stirring is carried for 6 hours at 50° C. and the mixture is allowed to cool to room temperature. After neutralization with sodium bicarbonate solution, the excess benzyl alcohol is distilled off under greatly reduced pressure 0 and the residue is purified by flash chromatography over silica gel using 9:1 n-hexane/ethyl acetate. After the solvent has been distilled off, 6.5 g of a colorless oil remain.

Workup

  1. distillationAfter neutralization with sodium bicarbonate solution, the excess benzyl alcohol is distilled off under greatly reduced pressure 0
  2. customthe residue is purified by flash chromatography over silica gel using 9:1 n-hexane/ethyl acetate
  3. distillationAfter the solvent has been distilled off

Sources & evidence

ORD record
ord-75bc565b159a47818aea009c6a23f005
Source dataset
uspto-grants-1997_12
Patent number
US05703017

Reaction notes

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