Methanol → Ethyl 3-Hydroxybutyrate

HRID 1638415Notes

Reaction equation

HRID 1638415 reaction equation
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].CO>[H][H]>[OH:4][CH:3]([CH3:5])[CH2:2][C:1]([O:7][CH2:8][CH3:9])=[O:6]

Participants

4

Reactant 2

HCID 887MethanolHCID 8868Ethyl Acetoacetate

Product 1

HCID 62572Ethyl 3-HydroxybutyrateYield 26%

Reagents, catalysts & solvents 1

HCID 178418361HCID 178418361, compoundSolvent

Procedure

To 3.90 g of ethyl acetoacetate were added 7.4 mg of rhodium 1,5-cyclooctadiene chloride complex compound, 22.1 mg of BCPM and 10 ml of methanol, and the mixture was charged into an autoclave. The mixture was stirred in the autoclave for 45 hours at 50° C. in hydrogen atmosphere at an initial pressure of 50 atm. It was confirmed by gas chromatography that 100% of the starting material had been converted. After distilling off the solvent, ethyl β-hydroxybutyrate was obtained almost theoretically by distillation under reduced pressure. [α]D23 =-2.67° (neat) (optical yield: 26%).

Workup

  1. additionthe mixture was charged into an autoclave
  2. distillationAfter distilling off the solvent

Sources & evidence

ORD record
ord-e67e31ce86244196adb1bde3001384e7
Source dataset
uspto-grants-1989_11
Patent number
US04879389

Reaction notes

Loading…