Methyl Acrylate → Methyl Cinnamate

Temperature

100 °C

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%.

1. customobtained in Example 2
2. washThe organic layers were then washed with brine
3. dry with materialdried over sodium sulfate
4. customThe solvents were removed under reduced pressure
5. customthe resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1)

ORD record

ord-b6d18ad61dea494884e202cba55103f3

Source dataset

uspto-grants-2006_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07122848B2