2,2-Dimethyl-1,3-cyclohexanedione → 3-Hydroxy-2,2-dimethylcyclohexan-1-one

HRID 1749531Notes

Reaction equation

HRID 1749531 reaction equation
[CH3:1][C:2]1([CH3:10])[C:7](=[O:8])[CH2:6][CH2:5][CH2:4][C:3]1=[O:9].[BH4-].[Na+]>CO>[OH:9][CH:3]1[CH2:4][CH2:5][CH2:6][C:7](=[O:8])[C:2]1([CH3:10])[CH3:1]

Participants

4

Reactant 2

HCID 5509672,2-Dimethyl-1,3-cyclohexanedioneHCID 4311764Sodium borohydride

Product 1

HCID 134975473-Hydroxy-2,2-dimethylcyclohexan-1-oneYield 78.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2,2-dimethylcyclohexane-1,3-dione (2.00 g, 14.3 mmol) in MeOH (20 mL) was added sodium borohydride (135 mg, 3.58 mmol) portion-wise at 0° C. The resulting solution was stirred at room temperature for 1 hour. The reaction was quenched with water and the mixture was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated to afford the title compound (1.6 g, crude). MS (ESI) m/z 143.2 [M+H]+.

Workup

  1. customThe reaction was quenched with water
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-02c226cce4294474b7142227d4fa7291
Source dataset
uspto-grants-2015_10
Patent number
US09156798B2

Reaction notes

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