Methanol → HCID 15218719, compound

HRID 2226692Notes

Reaction equation

HRID 2226692 reaction equation
[C:1]1([CH2:7][C:8](=[O:14])[CH2:9][CH2:10][C:11](=[O:13])[CH3:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO>C(Cl)Cl>[OH:14][CH:8]([CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[CH2:9][CH2:10][C:11](=[O:13])[CH3:12]

Participants

4

Reactant 2

HCID 887MethanolHCID 10035428HCID 10035428, compound

Product 1

HCID 15218719HCID 15218719, compoundYield 60.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 100-ml stainless steel autoclave purged with nitrogen in advance was charged with 5 g (0.0261 mol) of 6-phenyl-2,5-hexanedione and 10 ml of methanol. A solution of 0.185 g (0.13 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 36 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 3.03 g of (-)-5-hydroxy-6-phenylhexane-2-one (yield: 60.2%).

Workup

  1. customA 100-ml stainless steel autoclave purged with nitrogen in advance
  2. customreaction at a reaction temperature of 50° C. for 36 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-80eb09321d5743419d88fb4cb59421ba
Source dataset
uspto-grants-1994_09
Patent number
US05349107

Reaction notes

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