Ethanol → Ethyl methoxycinnamate

Participants

Reaction Conditions

Reaction Steps

Compounds 100, 105, 107, and 106 were synthesized under the Corey-Chaykovsky cyclopropanation reaction conditions (TMSOI, NaH, DMSO). A mixture of trans-4-methoxycinnamic acid (18 g, 101 mmol) and concentrated H2SO4 (0.5 mL) in absolute EtOH (100 mL) was refluxed at 90° C. (bath temperature) for 16 h. After the excess EtOH was removed by a rotary evaporator, the residue was treated with H2O (100 mL), and the resulting mixture was extracted with ether (3×120 mL). The combined extracts were washed with 1N aq. NaOH (2×50 mL), H2O (80 mL) and brine (80 mL), and dried (anhydrous Na2SO4). The solvent was evaporated to dryness to give ethyl trans-4-methoxycinnamate (20 g, 96% yield) as light yellow oil.

Provenance & Evidence