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

HRID 378361Notes

Reaction equation

HRID 378361 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

Conditions

Temperature
50 °C

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. The mixture is stirred at 50° C. for 6 hours and allowed to cool to room temperature. After neutralization with sodium bicarbonate solution, the excess benzyl alcohol is removed by distillation under high vacuum, and the residue is purified by flash chromatography on silica gel with 9:1 n-hexane/ethyl acetate. After removal of the solvent by distillation, 6.5 g of a colorless oil remain.

Workup

  1. temperatureto cool to room temperature
  2. customAfter neutralization with sodium bicarbonate solution, the excess benzyl alcohol is removed by distillation under high vacuum
  3. customthe residue is purified by flash chromatography on silica gel with 9:1 n-hexane/ethyl acetate
  4. customAfter removal of the solvent
  5. distillationby distillation, 6.5 g of a colorless oil

Sources & evidence

ORD record
ord-ec22ef5365b144248f249b920c5151a0
Source dataset
uspto-grants-2000_02
Patent number
US06030975

Reaction notes

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