Benzyl Alcohol → HCID 86665009, compound

Participants

Reaction Steps

A mixture of 14 (23.4 g, 109.5 mmol), p-toluenesulfonic acid monohydrate (62.5 g, 328.5 mmol), and benzyl alcohol (56.7 mL, 547.4 mmol) in CHC13 (320 mL) was refluxed for 4 h by using a Soxhlet apparatus containing dry silica gel. After cooling, CHC13 was evaporated and an equal volume of diethyl ether was added to the residue. The resulting ppt was collected by filtration, washed with ether, and air-dried to provide 15 as a white solid (38.0 g, 79%). 1H NMR (400 MHz, DMSO-d6) δ 8.58 (br s, 3H), 7.45 (m, 7H), 7.11 (d, 2H), 5.24 (AB, 2H), 4.38 (t, 1H), 3.00 (d, 2H), 2.29 (s, 3H), 1.26 (s, 9H).

Provenance & Evidence