1-Dodecanol → Dodecyl 2-bromopropanoate

Temperature

57.5 °C

To a stirred solution of 1-decanol 2 (10 g, 53.7 mmol) in toluene (100 mL) was added triethylamine (7.5 mL, 53.7 mmol)) and followed by 2-bromo propionyl bromide 58 (12.7 g, 59.1 mmol) at 5-10° C. The reaction mixture was stirred for 3 hour at 55-60° C., and the reaction was monitored by TLC. The reaction mixture was quenched with saturated sodium bicarbonate solution and stirred for 15 minutes at 25-35° C. The aqueous and organic layers were separated, the organic layer was washed with brine, and the combined organic layers were washed with brine solution. The organic layer was dried over Na2SO4 and concentrated under vacuum to afford crude 59 (16.2 g, yield: 94%) as a liquid.

1. customThe reaction mixture was quenched with saturated sodium bicarbonate solution
2. stirringstirred for 15 minutes at 25-35° C
3. customThe aqueous and organic layers were separated
4. washthe organic layer was washed with brine
5. washthe combined organic layers were washed with brine solution
6. dry with materialThe organic layer was dried over Na2SO4
7. concentrationconcentrated under vacuum

ORD record

ord-6983ec8315074454a9cd88da83c107a6

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08900625B2