Benzyl Bromide → HCID 86653775, compound

Temperature

60 °C

A solution of 2,3,5-trimethylhydroquinone (15.2 g, 100 mmol) in DMF (150 mL) was treated with BnBr (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 BnBr (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 EtOAc and the combined filtrates washed with 500 mL H2O. The aqueous layer was extracted 4×250 mL EtOAc 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 1,4-bis(benzyloxy)-3,5,6-trimethylbenzene as a brown solid

1. temperatureheated to 60° C. for an additional 48 h
2. temperatureThe reaction was cooled
3. filtrationfiltered through Celite
4. washthe filter cake rinsed 2×100 mL EtOAc
5. washthe combined filtrates washed with 500 mL H2O
6. extractionThe aqueous layer was extracted 4×250 mL EtOAc
7. concentrationconcentrated at 80° C. by rotary evaporation
8. additionThe brown residue was poured onto 300 mL water which
9. customprecipitated a light brown solid
10. filtrationThe brown solid was collected by filtration
11. washwashed with 2×50 mL H2O
12. customdried

ORD record

ord-5cb0f403d3844cd9994c9a7ff2ab2758

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08716486B2