Sodium Bicarbonate → Cyclohexanecarboxylic acid, 4-(hydroxymethyl)-, methyl ester

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Reaction Steps

To a mixture of (4-benzyloxymethyl-cyclohexyl)-methanol (1.40 g, 6 mmol) in dichloromethane (28 mL) is added Dess-Marin reagent (2.53 g, 6 mmol) at 0° C., and the mixture is stirred for 0.5 hour while warming 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-cyclohexanecarbaldehyde, is obtained (1.07 g, 79%) after purification using silica gel column chromatography (eluent: EtOAc/hexane).

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