Water → 1-Methyl-3-methylidenecyclobutane-1-carboxylic acid

To a solution of KOH (12.0 g, 213 mmol) in water (10 mL) and EtOH (10 mL) was added 1-methyl-3-methylidenecyclobutanecarbonitrile (53.3 mmol, crude) and the resulting solution was heated to reflux for 2.5 hrs. The mixture was cooled to rt and the solvent was removed under vacuum. The residue was diluted with water (30 mL) and washed with EtOAc (30 mL). The aqueous layer was acidified with concentrated HCl to pH˜1 in ice bath, and then extracted with EtOAc (two×30 mL). The combined organics were dried over MgSO4 and concentrated to give the title compound acid as pale brown liquid. 1H NMR (400 MHz, chloroform-d) δ ppm 4.90 (quin, J=2.41 Hz, 2H), 3.16-3.34 (m, 2H), 2.54 (qd, J=2.10, 16.57 Hz, 2H), 1.49 (s, 3H).

1. temperaturethe resulting solution was heated
2. temperatureto reflux for 2.5 hrs
3. customthe solvent was removed under vacuum
4. additionThe residue was diluted with water (30 mL)
5. washwashed with EtOAc (30 mL)
6. extractionextracted with EtOAc (two×30 mL)
7. dry with materialThe combined organics were dried over MgSO4
8. concentrationconcentrated

ORD record

ord-2b96e0dc5cbf47b5a4b727079d5b47fa

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09040547B2