4-Benzyloxymethyl-cyclohexanecarboxylic acid methyl ester → HCID 178501147, compound

HRID 217239Notes

Reaction equation

HRID 217239 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]([C@H:5]1[CH2:10][CH2:9][C@H: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 178501147HCID 178501147, compoundYield 72%

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 presence of catalytic amount of 10% Pd/C, the reaction mixture is stirred for 3 hours under hydrogen (10 bar). After removing 10% Pd/C, solvent is evaporated to obtain trans-4-hydroxymethyl-cyclohexanecarboxylic acid methyl ester as colorless oil (160 mg, 72%) after purification. 1H-NMR (400 MHz, CDCl3), δ (ppm): 0.99 (m, 2H), 1.47 (m, 3H), 1.88 (m, 2H), 2.02 (m, 2H), 2.23 (m, 1H), 3.46 (d, 2H), 3.66 (s, 3H).

Workup

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

Sources & evidence

ORD record
ord-a9d01d05b12c44d38746f16eadcb9a7b
Source dataset
uspto-grants-2012_06
Patent number
US08193349B2

Reaction notes

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