4-Benzyloxymethyl-cyclohexanecarboxylic acid methyl ester → Cyclohexanecarboxylic acid, 4-(hydroxymethyl)-, methyl ester

HRID 409487Notes

Reaction equation

HRID 409487 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][CH:8]([CH2:11][O:12]CC2C=CC=CC=2)[CH2:7][CH2:6]1)=[O:4]>CO.[Pd]>[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][CH:8]([CH2:11][OH:12])[CH2:7][CH2:6]1)=[O:4]

Participants

4

Reactant 1

HCID 576866884-Benzyloxymethyl-cyclohexanecarboxylic acid methyl ester

Product 1

HCID 11073869Cyclohexanecarboxylic acid, 4-(hydroxymethyl)-, methyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4-Benzyloxymethyl-cyclohexanecarboxylic acid methyl ester (340 mg, 1.30 mmol) is dissolved in MeOH (15 mL). In the presence of catalytic amount of 10% Pd/C, the reaction mixture is stirred for 3 hours under H2 (10 bar). After removal of 10% Pd/C, solvent is evaporated. The desired product, 4-hydroxymethyl-cyclohexanecarboxylic acid methyl ester, is obtained (160 mg, 72%) after purification using silica gel column chromatography (eluent: EtOAc/hexane).

Workup

  1. customAfter removal of 10% Pd/C, solvent
  2. customis evaporated

Sources & evidence

ORD record
ord-542503f5f7854087a5604f6b46d59ab0
Source dataset
uspto-grants-2014_06
Patent number
US08759365B2

Reaction notes

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