Sodium Hydroxide → 2-(4-Chlorophenyl)-2-cyclopropylacetic acid

A mixture of 13.0 grams (0.058 mole) of methyl 2-cyclopropyl-2-(4-chlorophenyl)acetate and 5.0 grams of an aqueous, 50% sodium hydroxide solution in 50 mL of methanol was stirred at ambient temperature for 18 hours. The reaction mixture was diluted with 150 mL of water, and the solution was decanted from a solid residue. The liquid portion was washed with three portions of diethyl ether. The combined ether washes were, in turn, washed with an aqueous, dilute sodium hydroxide solution. The combined aqueous layers were made acidic by the slow addition of aqueous, 10% hydrochloric acid. The acidified mixture was extracted with five portions of methylene chloride. The combined extracts were dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure, yielding 7.4 grams of 2-cyclopropyl-2-(4-chlorophenyl)acetic acid as a solid, m.p. 95°-96° C.

1. customthe solution was decanted from a solid residue
2. washThe liquid portion was washed with three portions of diethyl ether
3. washwashed with an aqueous, dilute sodium hydroxide solution
4. additionThe combined aqueous layers were made acidic by the slow addition of aqueous, 10% hydrochloric acid
5. extractionThe acidified mixture was extracted with five portions of methylene chloride
6. dry with materialThe combined extracts were dried with sodium sulfate
7. filtrationfiltered
8. concentrationThe filtrate was concentrated under reduced pressure

ORD record

ord-7d3cc1e343d04b4d974111562fa9b98e

Source dataset

uspto-grants-1989_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04808762