Benzyl Bromide → HCID 86653775, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2,3,5-trimethylbenzene-1,4-diol (15.2 g, 100 mmol) in DMF (150 mL) was treated with benzyl bromide (35.7 mL, 51.6 g, 300 mmol, 3 equiv.) and anhydrous K2CO3 (55.3 g, 400 mmol, 4 equiv.). The brown suspension was heated to 60° C. for 48 h at which time the reaction was judged incomplete by HPLC. Additional benzyl bromide (37 mL, 300 mmol, 3 equiv.) and K2CO3 (50 g, 362 mmol, 3.6 equiv.) were added and heated to 60° C. for an additional 48 h. The reaction was cooled, filtered through Celite, the filter cake rinsed 2×100 mL ethyl acetate and the combined filtrates washed with 500 mL H2O. The aqueous layer was extracted 4×250 mL ethylacetate and concentrated at 80° C. by rotary evaporation. The brown residue was poured onto 300 mL water which precipitated a light brown solid and the resulting suspension stirred overnight. The brown solid was collected by filtration, washed with 2×50 mL H2O and dried, yielding 26.8 g of 2,5-bis(benzyloxy)-3,4,6-trimethylbenzene as a brown solid. 1H NMR (400 MHz, CDCl3) δ=7.50-7.34 (m, 10 H), 6.64 (s, 1 H), 5.03 (s, 2 H), 4.74 (s, 2 H), 2.30 (s, 3 H), 2.25 (s, 3 H), 2.20 (s, 3 H) ppm.

Provenance & Evidence