Methanol → Methyl 11-bromoundecanoate

A mixture of 13.25 g of 11-bromoundecanoic acid, 100 mL of methanol and 10 drops of hydrochloric acid was stirred for 3 days in a closed flask. The solvent was removed in vacuo and the residual oil was redissolved in ether (100 mL). This solution was subsequently washed twice with 25 mL of a saturated NaHCO3 solution, once with water (25 mL) and once with brine (25 mL). Drying over sodium sulfate and removal of the solvents in vacuo gave 13.32 g of the product as a yellowish oil, which was sufficiently pure to use in the next step. 1H NMR (200 MHz, CDCl3): δ 3.65 (s, 3H); 3.39 (t, 2H); 2.28 (t, 2H); 1.90-1.78 (m, 2H); 1.70-1.50 (m, 2H); 1.50-1.21 (m, 12H) ppm. IR (neat, cm−1): 2928 (m); 2855 (m); 1741 (s).

1. customThe solvent was removed in vacuo
2. dissolutionthe residual oil was redissolved in ether (100 mL)
3. washThis solution was subsequently washed twice with 25 mL of a saturated NaHCO3 solution, once with water (25 mL) and once with brine (25 mL)
4. dry with materialDrying over sodium sulfate and removal of the solvents in vacuo

ORD record

ord-9a4999b1b7c549ac9a727105f0187d7f

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08580810B2