Water → 3-(3-Methylphenylthio)propanoic Acid

A solution of 22.0 grams (0.105 mole) of methyl 3-(3-methylphenylthio)propanoate in 200 mL of methanol was stirred, and 40 mL of aqueous 10% potassium hydroxide was added. Upon completion of addition, the reaction mixture was stirred at ambient temperature during an 18 hour period. GC analysis of the reaction mixture indicated that the reaction was not complete. An additional 30 mL of the aqueous 10% potassium hydroxide was added, and the reaction mixture was stirred for an additional three hours. After this time, 100 mL of water was added to the reaction mixture and the methanol was removed under reduced pressure. The residue was washed with three 50 mL portions of diethyl ether. The cooled residue was then acidified with aqueous 10% hydrochloric acid, and extracted with 100 mL of diethyl ether. The extract was dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to an oily residue. The residue was stirred with hexane and cooled, resulting in a solid material being formed. The solid was collected by filtration and dried, yielding 17.0 grams of the subject compound. The NMR spectrum was consistent with the proposed structure.

1. additionUpon completion of addition
2. stirringthe reaction mixture was stirred for an additional three hours
3. customthe methanol was removed under reduced pressure
4. washThe residue was washed with three 50 mL portions of diethyl ether
5. extractionextracted with 100 mL of diethyl ether
6. dry with materialThe extract was dried with sodium sulfate
7. filtrationfiltered
8. concentrationThe filtrate was concentrated under reduced pressure to an oily residue
9. stirringThe residue was stirred with hexane
10. temperaturecooled
11. customresulting in a solid material
12. custombeing formed
13. filtrationThe solid was collected by filtration
14. customdried

ORD record

ord-7a3790e4377c4ef9abe3fb8126258e8a

Source dataset

uspto-grants-2008_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07417057B2