Methyl Acrylate → HCID 21841221, compound

Participants

Reaction Steps

A mixture of 5.2 g of 6-bromo-2-(6-hydroxyhexyloxy)naphthalene, 25 ml of triethylamine, 4.3 ml of methyl acrylate, 0.072 g of palladium acetate and 0.392 g of tri-o-tolylphosphine was heated under reflux for 16 hrs. In order to complete the reaction, a further 0.177 g of palladium acetate, 2.5 g of tetrabutylammonium bromide, 10 ml of dimethylformamide and 2 ml of methyl acrylate were added and the mixture was heated to reflux for a further 24 hrs. Thereafter, the reaction mixture was cooled, partitioned between ethyl acetate and water, the organic phase was washed with water, and dried over magnesium sulphate, filtered and evaporated. The residue was chromatographed on 250 g of silica gel with toluene/ethyl acetate (3:1 to 1:1) and subsequently crystallized twice from toluene. This gave 0.63 g of methyl (E)-3-[6-(6-hydroxyhexyloxy)naphthalen-2-yl]acrylate as a colorless solid, λmax. (CH2Cl2): 326 nm (ε=27660).

Provenance & Evidence