Methanol → 4-Hydroxy-1-phenyl-1-pentanone

HRID 2226690

Reaction equation

HRID 2226690 reaction equation
[C:1]1([C:7](=[O:13])[CH2:8][CH2:9][C:10](=[O:12])[CH3:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO>C(Cl)Cl>[OH:12][CH:10]([CH3:11])[CH2:9][CH2:8][C:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:13]

Participants

4

Reactant 2

HCID 887MethanolHCID 1363711-Phenyl-1,4-pentanedione

Product 1

HCID 1548894-Hydroxy-1-phenyl-1-pentanoneYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 100-ml stainless steel autoclave purged with nitrogen in advance was charged with 5 g (0.0284 mol) of 5-phenyl-2,5-pentanedione and 10 ml of methanol. A solution of 0.2 g (0.142 mmol) of [RuI(p-cymene)((R)-T-BINAP)]I3 in 2 ml of methylene chloride was added thereto, thereby conducting reaction at a reaction temperature of 50° C. for 40 hours under a hydrogen pressure of 50 kg/cm2. After distilling off the solvent, the residue was purified by column chromatography on a silica gel using a developing solvent of hexane/ethyl acetate (5/1) to obtain 4.5 g of (-)-4-hydroxy-1-phenylpentane-1-one (yield: 90.0%).

Workup

  1. customA 100-ml stainless steel autoclave purged with nitrogen in advance
  2. customreaction at a reaction temperature of 50° C. for 40 hours under a hydrogen pressure of 50 kg/cm2
  3. distillationAfter distilling off the solvent
  4. customthe residue was purified by column chromatography on a silica gel using a developing solvent of hexane/ethyl acetate (5/1)

Sources & evidence

ORD record
ord-ed37c936785b4937af54c0a65986c3cd
Source dataset
uspto-grants-1994_09
Patent number
US05349107

Linked notes

Loading…