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

HRID 356865Notes

Reaction equation

HRID 356865 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-afe9f54ad3f14695a2cdf9ae4e5dd264
Source dataset
uspto-grants-1998_11
Patent number
US05840722

Reaction notes

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