Sulfuric Acid → 2,2-Dimethylchroman

Participants

Reaction Steps

A mixture of 16 g (89 mmol) of 4-(2-hydroxyphenyl)-2-methyl-2-butanol, (Compound 55), 40 ml of conc. H2SO4 and 160 ml of water was heated at reflux for 4 hours. The mixture was cooled, diluted with 300 ml of water and extracted with 2×100 ml of hexane. The organic extracts were combined, washed successively with water and saturated NaCl solution and then dried. The solution was then filtered and the filtrate concentrated in-vacuo to give the title compound as a yellow oil. PMR (CDCl3) : & 1.32 (6H, s), 1.78 (2H, t, J~6.8 Hz), 2.76 (2H, t, J~6.8 Hz), 6.74-6.85 (2H, m), 7.01-7.12 (2H, m).

Provenance & Evidence