Methanol → 2-(4-Chlorophenyl)cyclopropanecarboxylic acid

Ethyl 2-(4-chlorophenyl)-cyclopropanecarboxylate (0.210 g, 0.935 mmol) was placed in a 50 ml flask and dissolved in EtOH (5 ml). NaOMe in MeOH (25%, 0.808 g, 3.74 mmol) was added to the mixture. The mixture was heated for 17 hours under reflux and then concentrated. The residue was dissolved in MeOH (10 ml), and 1M solution of LiOH—H2O (3.74 ml, 3.74 mmol) was added. The methanol was removed under reduced pressure. The residue was diluted with water (10 ml) and washed with EtOAc (10 ml). The aqueous layer was acidified by 1N HCl (10 ml) to pH 1 and a solid precipitated out of solution. The mixture was extracted with EtOAc (3×10 ml) and the combined extracts were dried over MgSO4, filtered, and concentrated to provide 181 mg of the title compound as a solid (98%). The crude solid was used in the next step without further purification.

1. temperatureThe mixture was heated for 17 hours
2. temperatureunder reflux
3. concentrationconcentrated
4. dissolutionThe residue was dissolved in MeOH (10 ml)
5. customThe methanol was removed under reduced pressure
6. additionThe residue was diluted with water (10 ml)
7. washwashed with EtOAc (10 ml)
8. customa solid precipitated out of solution
9. extractionThe mixture was extracted with EtOAc (3×10 ml)
10. dry with materialthe combined extracts were dried over MgSO4
11. filtrationfiltered
12. concentrationconcentrated

ORD record

ord-55e4296ff73f41ac8944f762ddab1131

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09096567B2