Acetic Anhydride → 1,1-Cyclohexanediacetic acid mono methyl ester

A solution of 1,1-cyclohexanediacetic acid (5.0 g) in acetic anhydride (8.0 mL) was stirred under reflux for 5 hours. The solution was then concentrated under reduced pressure and distilled with toluene azeotropically. To a solution of the resulting residue in methanol (15.2 mL) was added boron trifluoride diethyl ether complex (1.58 mL) at room temperature. The solution was stirred at room temperature for 2 hours. Saturated aqueous sodium carbonate solution was added to the solution and it was washed with diethyl ether. The aqueous layer was neutralized by addition of conc. hydrochloric acid and then extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride solution, and then, dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to give the title compound (4.21 g).

1. temperatureunder reflux for 5 hours
2. concentrationThe solution was then concentrated under reduced pressure
3. distillationdistilled with toluene azeotropically
4. additionTo a solution of the resulting residue in methanol (15.2 mL) was added boron trifluoride diethyl ether complex (1.58 mL) at room temperature
5. additionSaturated aqueous sodium carbonate solution was added to the solution and it
6. washwas washed with diethyl ether
7. additionThe aqueous layer was neutralized by addition of conc. hydrochloric acid
8. extractionextracted with ethyl acetate
9. washThe organic layer was washed with saturated aqueous sodium chloride solution
10. dry with materialdried over anhydrous magnesium sulfate
11. distillationThe solvent was distilled off under reduced pressure

ORD record

ord-42827a07d81f48fe98b5a3397ba75e34

Source dataset

uspto-grants-2008_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07375115B2