Methyl Acrylate → Methyl Cinnamate

Participants

Reaction Conditions

Reaction Steps

To a solution of iodobenzene (102 mg), methylacrylate (1.25 eq.) and triethylamine (1.25 eq.) in acetonitrile (3.00 ml) was added the catalyst substrate (5×5) obtained in Example 2. The mixture was stirred at 100° C. for 12 h under an argon atmosphere. The organic layers were then washed with brine and dried over sodium sulfate. The solvents were removed under reduced pressure and the resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1). The intended product, trans-methyl cinnamate was obtained with yield of 35%. The recycled substrate was subjected to the above reaction conditions in a 2nd run and the intended product methyl cinnamate was obtained with yield of 13%. Further conducted the 3rd run and the intended methyl cinnamate was obtained with yield of 9%.

Provenance & Evidence