Methyl 3-(3-cyclohexenyl)-5-chlorosalicylate → Methyl 2-chloro-trans-5a,6,7,8,9,9a-hexahydrodibenzofuran-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of 9 g of methyl 3-(3-cyclohexenyl)-5-chlorosalicylate and 20 ml trifluoroacetic acid is heated at 70° C. overnight. The cooled reaction mixture is diluted with hexanes, washed three times with water, dried and evaporated to dryness. The residue is purified with flash chromatography using 10% ethyl acetate/hexane to give four fractions. First fraction 2.29 of material (mixture of at least two materials); second fraction 2.29 cis isomer; third fraction 1.69 mixture of cis and trans isomers; and fourth fraction 19 trans isomer.

Provenance & Evidence