Hydroquinone → HCID 131726869, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of ethyl(2E)-4-methylpenta-2,4-dienoate (8.5 g, 60.6 mmol), acrolein (5.1 g, 91 mmol) and hydroquinone (67 mg, 0.6 mmol) was heated to 95-100° C. for 24 h. The mainly cis-ethyl 6-formyl-3-methylcyclohex-2-ene-1-carboxylate was isolated by distillation (60-80° C./0.5 mm Hg) and then equilibrated with freshly activated basic alumina (−2 grams of basic alumina per gram of cis-ethyl 6-formyl-3-methylcyclohex-2-ene-1-carboxylate) in benzene as solvent (−6 mL benzene per gram of cis-ethyl 6-formyl-3-methylcyclohex-2-ene-1-carboxylate). After stirring at room temperature for 6 days, the equilibration mixture was filtered through Celite™ and the filter cake was washed with ethyl acetate. (1R/S,6R/S)-Ethyl 6-formyl-3-methylcyclohex-2-ene-1-carboxylate was then purified by distillation (65° C./15 mm Hg) as a colorless oil.

Provenance & Evidence