Methanol → Methyl 6-Bromohexanoate

Temperature

25 °C

To a 2 liter round bottom flask, charge with 99.7 g (0.511 mol) of 6-bromohexanoate (Aldrich Chemical Co., Milwaukee, Wis.) and 1 liter of methanol, was bubbled hydrogen chloride gas for 1-2 minutes. The mixture was stirred at 20-30° C. for 18 h and then concentrated via rotary evaporation. The residue was diluted with 500 mL of diethyl ether and washed with 150 mL of de-ionized water, 200 mL of saturated sodium bicarbonate, and then once again with 200 mL of de-ionized water. The organic phase was dried over anhydrous magnesium sulfate, filtered and concentrated via rotary evaporation. The residue was distilled under vacuum to afford 99.6 g of the product (1) as a colorless oil (93%): b.p.=93-96° C. at 3 mm Hg: 1H NMR (d6-DMSO) d 3.57 (3H, 5), 3.51 (2H, t), 2.30 (2H, t), 1.78 (2H, pentet) and 1.62-1.28 (4H, m) ppm.

1. customwas bubbled hydrogen chloride gas for 1-2 minutes
2. concentrationconcentrated via rotary evaporation
3. additionThe residue was diluted with 500 mL of diethyl ether
4. washwashed with 150 mL of de-ionized water, 200 mL of saturated sodium bicarbonate
5. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated via rotary evaporation
8. distillationThe residue was distilled under vacuum

ORD record

ord-8009bbb96709434d9beeac83732cc79e

Source dataset

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07744853B2