Dimethylformamide → Ethyl 4-ethoxy-3-methylbenzoate

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-hydroxy-3-methyl-benzoic acid (1.00 g, 6.57 mmol) in N,N-dimethylformamide (10 mL) was added potassium carbonate (2.73 g, 19.7 mmol) and bromoethane (3.58 g, 2.44 mL, 32.9 mmol). The reaction mixture heated at 45° C. for 48 h in a sealed tube. The reaction mixture allowed to cool then diluted with water and ether. The ether layer was washed with 50% saturated NaHCO3 (50 mL) and brine (50 mL), dried over Na2SO4, and concentrated in vacuo to provide ethyl 4-ethoxy-3-methylbenzoate as an orange-colored oil. The crude product was taken directly to the next step. ESI-MS m/z calc. 208.10994. found 209.3 (M+1)+; Retention time: 1.78 minutes (3 min run).

Provenance & Evidence