Ethyl orthoformate → HCID 54151626, compound

Participants

Reaction Steps

A solution of 0.706 g of 4'-(6-acryloxyhexyloxy)biphenyl-4-carboxaldehyde, 1 ml of orthoformic acid triethyl ester, 0.7 ml of diethyl L-tartrate, 27 mg of BHT, 6.8 mg of 4-toluenesulphonic acid monohydrate and 10 ml of toluene was allowed to stand for 1 hour at room temperature, then heated for 2.5 hours to boiling, the solvent being distilled off and replaced by fresh toluene. After the addition of 3 drops of triethylamine and cooling, it was diluted with diethyl ether, washed with water, dried over sodium sulphate, filtered and concentrated at 40° C. in vacuo. The oily residue was chromatographed on 45 g of silica gel with hexane/ethyl acetate 4:1. Recrystallisation from ethyl acetate resulted in 0.18 g (4R,5R)-2-[4-(6-acryloxyhexyloxy)biphenyl-4-yl]-1,3-dioxolane-4,5-dicarboxy acid diethyl ester; boiling point (C-I) 65° C.

Provenance & Evidence