methyl 4-(hydroxymethyl)cyclohexane-1-carboxylate

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

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). After removal of 10% Pd/C, solvent is evaporated

Conditions: temp:2.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-Benzyloxymethyl-cyclohexanecarbaldehyde (1.70 g, 2.0 mmol) is dissolved in acetic acid (0.24 mL) and 2 mL of MeOH. The reaction mixture is cooled to 0-5° C. and stirred while 10% NaOCl solution (2.5 mL, 4 mmol) is added dropwise over 20 minutes. The cooling bath is removed and the mixture is allowed to come to room temperature. After addition of saturated aqueous NaHCO3, the aqueous layer is extracted with EtOAc. The combined organic layer (dried with MgSO4) is concentrated. The desired product, 4-benzyloxymethyl-cyclohexanecarboxylic acid methyl ester, is obtained (343 mg, 65%) after purification using silica gel column chromatography (eluent: EtOAc/hexane). is added dropwise over 20 minutes The cooling bath is removed to come to room temperature After addition of saturated aqueous NaHCO3 the aqueous layer is extracted with EtOAc The combined organic layer (dried with MgSO4) is concentrated