Methanol → 2-Hydroxynonan-5-one

HRID 2226691Notes

Reaction equation

HRID 2226691 reaction equation
[CH3:1][C:2](=[O:11])[CH2:3][CH2:4][C:5](=[O:10])[CH2:6][CH2:7][CH2:8][CH3:9].CO.CCN(CC)CC>C(Cl)Cl>[OH:11][CH:2]([CH2:3][CH2:4][C:5](=[O:10])[CH2:6][CH2:7][CH2:8][CH3:9])[CH3:1]

Participants

5

Reactant 3

HCID 887MethanolHCID 8471TriethylamineHCID 111265032,5-nonanedione

Product 1

HCID 131640882-Hydroxynonan-5-oneYield 65.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 100-ml stainless steel autoclave purged with nitrogen in advance was charged with 5 g (0.032 mol) of 2,5-nonanedione and 10 ml of methanol. A solution of 0.144 g (0.08 mmol) of Ru2Cl4 ((R)-T-BINAP)2 (NEt3) in 2 ml of methylene chloride was added thereto, thereby conducting reaction at a reaction temperature of 50° C. for 20 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 (4/1) to obtain 3.3 g of (-)-2-hydroxynonane-5-one (yield: 65.6%).

Workup

  1. customA 100-ml stainless steel autoclave purged with nitrogen in advance
  2. customreaction at a reaction temperature of 50° C. for 20 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 (4/1)

Sources & evidence

ORD record
ord-31fa6e32378547bd8716b9a909cc9238
Source dataset
uspto-grants-1994_09
Patent number
US05349107

Reaction notes

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