Water → Methyl 3-hydroxycyclohexane-1-carboxylate

HRID 340776

Reaction equation

HRID 340776 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][CH2:8][C:7](=[O:11])[CH2:6]1)=[O:4].[BH4-].[Na+].O.CCOC(C)=O>CO>[OH:11][CH:7]1[CH2:8][CH2:9][CH2:10][CH:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6]1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 566099Methyl 3-oxocyclohexane-1-carboxylateHCID 4311764Sodium borohydride

Product 1

HCID 12209242Methyl 3-hydroxycyclohexane-1-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

3-oxo-1-cyclohexanecarboxylic acid methyl ester (1.1 g, 7.04 mmol) was dissolved in methanol (25 ml) and cooled to 0° C. under N2. Sodium borohydride (0.550 g, 14.54 mmol) was added in portions and the resulting solution stirred at 0° C. for 2 h. The solution was then diluted by the dropwise addition of water, followed by EtOAc (100 mL). The aqueous phase was separated and extracted with EtOAc (2×50 ml). The combined organic layers were washed with brine, dried over sodium sulphate, and concentrated in vacuo to give the title compound. TLC: 40% EtOAc/hexanes, high Rf: 0.4, low Rf: 0.3.

Workup

  1. customThe aqueous phase was separated
  2. extractionextracted with EtOAc (2×50 ml)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-51efb87b148a4233b5eb57f52374eadc
Source dataset
uspto-grants-2014_11
Patent number
US08895596B2

Linked notes

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