Ethanol → 2-(3-(Propan-2-yloxy)phenyl)acetic acid

The title compound is prepared using known methods essentially as described in R. E. Counsel, et al., Journal of Medicinal Chemistry, 16:684-687 (1973) except that the benzyl chloride is replaced with 2-iodopropane. The 5-isopropoxyphenylacetonitrile thus prepared (15 grams) is dissolved in 160 ml of ethanol in the presence of 18 grams of potassium hydroxide. The resulting mixture is then refluxed for about two hours. The reaction mixture is then concentrated in vacuo and the residue is taken up in water and washed with diethyl ether. The aqueous phase is acidified with hydrochloric acid until the pH is 1, and extracted with diethyl ether. The extract is washed with water, dried over sodium sulfate, and filtered. The solvents are removed in vacuo and the residue is purified by chromatography on silica gel using methylene chloride/methanol (100/2 v/v) as the eluent to give the desired title product.

1. customThe title compound is prepared
2. temperatureThe resulting mixture is then refluxed for about two hours
3. concentrationThe reaction mixture is then concentrated in vacuo
4. washwashed with diethyl ether
5. extractionextracted with diethyl ether
6. washThe extract is washed with water
7. dry with materialdried over sodium sulfate
8. filtrationfiltered
9. customThe solvents are removed in vacuo
10. customthe residue is purified by chromatography on silica gel

ORD record

ord-6b746af9dc9e4ef29733d98efac78a4b

Source dataset

uspto-grants-1996_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05563133