Sodium Hydroxide → 1-(Methoxycarbonyl)cyclopropane-1-carboxylic acid

Temperature

0 °C

Dimethyl cyclopropane-1,1-dicarboxylate (26.08 mL, 189.87 mmol) is dissolved in methanol (319 mL) and the solution is cooled to 0° C. 1 N NaOH (190 mL, 190 mmol, 1 eq) in water is added dropwise. The resulting mixture is stirred at RT overnight. The solution is concentrated under reduced pressure to remove the methanol and the resulting aqueous solution is washed with dichloromethane (3×50 mL) and acidified with 1 N HCl (pH=2-3). The solution is then extracted with ethyl acetate (5×100 mL) and dichloromethane (3×50 mL). The combined organic portions are dried over MgSO4, filtered, and concentrated to afford the title compound (16.4 g, 60%). 1H NMR (400 MHz, CDCl3); δ 1.9-1.7 (m, 4H), 3.78 (s, 3H).

1. concentrationThe solution is concentrated under reduced pressure
2. customto remove the methanol
3. washthe resulting aqueous solution is washed with dichloromethane (3×50 mL)
4. extractionThe solution is then extracted with ethyl acetate (5×100 mL) and dichloromethane (3×50 mL)
5. dry with materialThe combined organic portions are dried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated

ORD record

ord-68223532941f4828b8a1b1979c60fd8c

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08288548B2