Water → HCID 67019287, compound

Participants

Reaction Steps

A solution of ketoenol 7 (68.0 g, 374 mmol), isobutanol (83.0 g, 1120 mmol), and p-toluenesulfonic acid (1.0 g, 1.2 mmol) in anhydrous benzene (730 mL) was refluxed overnight with azeotropic removal of water (Dean-Stark trap). The reaction mixture was cooled to room temperature, washed with saturated sodium bicarbonate solution (3×250 mL), brine (2×250 mL) and concentrated to give 88.0 g (98.9%) of 8 as a thick oil, which solidified upon cooling. MS m/z 239 (M+1); 1H NMR (300 MHz, CDCl3) δ 3.75 (d, 2H), 2.5 (t, 2H), 2.3-2.2 (m, 4H), 2.0-1.9 (m, 3H), 1.6-1.5 (m, 1H), 1.2-1.1 (m, 2H), 1.0 (d, 6H), 0.9 (d, 6H); 13C NMR (CDCl3) δ 198.4, 171.5, 120.1, 73.9, 38.0, 36.5, 28.8, 28.4, 25.5, 22.6, 21.1, 20.1, 19.1.

Provenance & Evidence