Methanol → Methyl 4-hydroxybicyclo(2.2.2)octane-1-carboxylate

To a solution of 4-hydroxybicyclo[2.2.2]octane-1-carboxylic acid (14 g, 82.4 mmol) in methanol (300 mL) was added concentrated sulfuric acid (1 mL). The mixture was refluxed for 10 h and then concentrated. The reside was dissolved in water (100 mL) and the mixture was extracted with ethyl acetate (200 mL×2). The combined organic phases were washed with saturated aqueous sodium hydrogen carbonate solution (100 mL), brine (100 mL) and dried over sodium sulfate. Concentration gave the title compound (14.5 g, yield 96%). 1H NMR (400 MHz, CDCl3) δ ppm 3.64 (s, 3H), 1.96-1.89 (m, 6H), 1.69-1.64 (m. 6H).

1. temperatureThe mixture was refluxed for 10 h
2. concentrationconcentrated
3. dissolutionThe reside was dissolved in water (100 mL)
4. extractionthe mixture was extracted with ethyl acetate (200 mL×2)
5. washThe combined organic phases were washed with saturated aqueous sodium hydrogen carbonate solution (100 mL), brine (100 mL)
6. dry with materialdried over sodium sulfate
7. concentrationConcentration

ORD record

ord-1eddfc7a2e09421b80cad2edec3cc40f

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09139534B2