Carbon Tetrachloride → 4-(3-Chloroprop-2-ynyl)phenylacetic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-(3-Hydroxyprop-2-ynyl)phenylacetic acid methyl ester (5.5 g, 0.027M) in tetrahydrofuran (110 ml) and carbon tetrachloride (110 ml) was added triphenylphosphine (7.81 g, 1.1 molar equivalents). The reaction mixture was heated at 60° C. for 3 h. After cooling, the solid obtained was removed by filtration and the mother liquors were concentrated under vacuum. The residue was purified by chromatography on silica gel using 50% diethyl ether in hexane as eluent to give the required product (5.35 g) as a colourless oil. δ (360 MHz, CDCl3) 3.62 (2H, s, CH2CO2CH3), 3.69 (3H, s, CH2CO2CH3), 4.36 (2H, s, CH2Cl), 7.23 (2H, d, J=8.2 Hz, ArH), 7.40 (2H, d, J=8.2 Hz, ArH).

Provenance & Evidence