4-Methylbenzoyl Chloride → HCID 67434527, compound

Participants

Reaction Steps

To a cooled (−78° C.) solution of ethyl 2-m-tolylacetate (1.697 g, 9.52 mmol) in THF (10.58 mL) was added LiHMDS (9.52 mL, 9.52 mmol). The reaction was stirred for 15 minutes and 4-methylbenzoyl chloride (1.546 g, 10 mmol) in THF (21.16 mL) was slowly added. The reaction was allowed to warm to room temperature over 2 h. The reaction was quenched with AcOH, diluted with water and extracted with EtOAc three times. The combined extracts were washed with brine, dried (MgSO4) and concentrated. The residue was purified by silica gel column chromatography to give the title compound as a yellow oil (2.213 g). 1H NMR (400 M Hz, CDCl3) δ ppm 1.24 (t, J=7.07 Hz, 3H), 2.33 (s, 3H), 2.37 (s, 3H), 4.15-4.28 (m, 2H), 5.54 (s, 1H), 7.10 (d, J=7.07 Hz, 1H), 7.16-7.25 (m, 5H), 7.85 (d, J=8.08 Hz, 2H).

Provenance & Evidence