Methyl Acrylate → 3-(4-Formyl-3,5-dimethylphenyl)-acrylic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

The above 4-amino-2,6-dimethylbenzaldehyde (1.0 g, 6.71 mmol) was taken up in enough 42% HBF4 until the suspension stirred well and then was cooled to 0° C. A solution of NaNO2 (463 mg, 6.71 mmol) in water (5 mL) was added slowly and after 30 min at 0° C., MeOH (20 mL) was added followed by Pd(OAc)2 (229 mg) and methyl acrylate (1.16 g, 13.42 mmol). The reaction mixture was heated at 80° C. for 30 min then the suspension was filtered through Celite and washed with CH2Cl2. The combined organic layers were washed with water, brine, dried with MgSO4, and filtered. The solvent was removed under reduced pressure and the residue was purified by flash chromatography using a 10/1 to 5/1 gradient of heptane/EtOAc to give 3-(4-formyl-3,5-dimethylphenyl)-acrylic acid methyl ester as a light yellow solid.

Provenance & Evidence