Acetyl chloride → 2,2-Dimethyl-6-acetylchroman

Participants

Reaction Steps

To a solution of 2,2-dimethylchroman (Compound 214, 15 g, 19.4 mmol) in dry CH2Cl2 (100 mL) was added acetyl chloride (1.52 ml, 21.3 mmol) followed by AlCl3 (2.84 g, 21.3 mmol). The reaction mixture was stirred at room temperature for 30 minutes and then poured into ice water. Extraction (CH2Cl2), drying (Na2SO4), and concentration under reduced pressure afforded a yellow oil. Column chromatography (EtOAc:hexanes 1:9) yielded 2.15 g (54%) of the title compound as a yellow solid. 1H NMR δ 7.73 (2H, m), 6.80 (1H, d, J=8.3 Hz), 2.83 (2H, t, J=6.9 Hz), 2.54 (3H, s), 1.84 (2H, t, J=6.9 Hz), 1.36 (6H, s). Anal. (C13H16O2) C, H.

Provenance & Evidence