Ethanol → Methyl 2-(3-hydroxycyclohexyl)acetate

HRID 420767Notes

Reaction equation

HRID 420767 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH2:4][CH:5]1[CH2:10][CH2:9][CH2:8][C:7](=[O:11])[CH2:6]1.C(O)C.[BH4-].[Na+]>C1COCC1>[CH3:1][O:2][C:3](=[O:12])[CH2:4][CH:5]1[CH2:10][CH2:9][CH2:8][CH:7]([OH:11])[CH2:6]1

Participants

5

Reactant 3

HCID 702EthanolHCID 5660952808-12-0HCID 4311764Sodium borohydride

Product 1

HCID 13071110Methyl 2-(3-hydroxycyclohexyl)acetateYield 100.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(3-Oxo-cyclohexyl)-acetic acid methyl ester (240 mg, 1.39 mmol) was dissolved in 5 ml THF and 5 ml ethanol and cooled to 0-5° C. Sodium borohydride (79 mg, 2.09 mmol) was added and the reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was quenched with saturated NaHCO3-solution and extracted three times with ethyl acetate. The organic extracts were washed with brine, dried with sodium sulfate, filtered and evaporated. The crude product (240 mg, 100%) was obtained as a light yellow oil and used without any further purification for the next step.

Workup

  1. customThe reaction mixture was quenched with saturated NaHCO3-solution
  2. extractionextracted three times with ethyl acetate
  3. washThe organic extracts were washed with brine
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-c56ba1ed153440ddbe52b93497056fe0
Source dataset
uspto-grants-2012_01
Patent number
US08097637B2

Reaction notes

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