Hydrochloric Acid → HCID 19384513, compound

Participants

Reaction Steps

A solution of 6.5 g of (E)-5-[2-(1,2,3,4-tetrahydro-9-octyl-9H-dibenzo [b,d]pyrrol-6-yl)ethenyl]-2-furancarboxylic acid methyl ester from Example 33 in 72 ml of methanol was treated with a solution of 4.9 g of 87% potassium hydroxide in 18 ml of water. The mixture was refluxed for 45 minutes, cooled, diluted with water, acidified with 2N HCl and then extracted with ethyl acetate. The organic phase was washed with water, dried over anhydrous magnesium sulfate and concentrated in vacuo to give 6.0 g of crude acid. Crystallization from ethyl acetate and hexane afforded 4.0 g (63.7%) of (E)-5-[2-(1,2,3,4-tetrahydro-9-octyl-9H-dibenzo[b,d]pyrrol-6-yl)ethenyl]-2-furancarboxylic acid as yellow crystals, mp 142°-144° C.

Provenance & Evidence