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

Participants

Reaction Conditions

Reaction Steps

To a suspension of 4-amino-2,6-dimethylbenzaldehyde (1.0 g., 6.71 mmol) in enough 42% HBF4 to be stirred at 0° C. was added a solution of NaNO2 (463 mg, 6.71 mmol) in water (5 mL) slowly. After 30 min at 0° C., MeOH (20 mL) was added followed by Pd(OAc)2 (229 mg) and methyl acrylate (1155 mg, 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 filtrate was extracted with CH2Cl2 and the organic layer was washed with water, brine, dried with MgSO4, and filtered. The solvent was removed under reduced pressure and the residue was purified by flash chromatography (heptane/EtOAc=10:1 to 5:1) to give the title compound. MS: m/z 219 (M+1).

Provenance & Evidence