Water → (1-Benzylcyclohex-2-en-1-yl)acetic acid

Participants

Reaction Conditions

Reaction Steps

To a mixture of NaH2PO4 (55.3 g), NaClO2 (36.3 g), DMSO (200 mL) and water (375 mL) was added a solution of 3-benzyl-3-formylmethylcyclohexene (57 g) in DMSO (150 mL) during a 3 hour period. After addition, the mixture was stirred overnight and diluted with ether (200 mL). This was extracted with saturated NaHCO3 (3×100 mL). The combined aqueous layer was cooled to 0° C. and acidified to PH=1 with conc. HCl. This was extracted with CH2Cl2 (3×300 mL). The combined organic layer was dried (Na2SO4) and the solvent was removed in vacuo. The residue was purified by column chromatography on silica gel to give the title compound as thick oil (50 g). MS (MH+=231).

Provenance & Evidence