Gamma-Butyrolactone → Butanoic acid, 4-(phenylthio)-

Sodium methoxide (1.2 equivalent) was added to 60 ml of ethanol, in one portion, and the suspension was stirred at room temperature. Thiophenol (1 equivalent) was added to the above suspension and stirred at room temperature for an additional 30 minutes. Butyrolactone (1.1 equivalent) was then added and the resulting mixture was stirred at reflux temperature for 6 hours, cooled to room temperature and concentrated in vacuo. The residual solid was washed with 200 ml hexane/ether 2:1, v/v. The solid was suspended in ice cold 2N HCl and stirred for 15 minutes. The solid was then filtered, washed with 100 ml hexane/ether and dried under reduced pressure at room temperature to give 4-(phenylsulfanyl)butanoic acid as a tan solid: 52% yield; 1H NMR (CDCl3) δ 7.32-7.12 (m, 5H), 2.94 (t, 2H, J=7.2 Hz), 2.41 (t, 2H, J=7.2 Hz), 1.85 (p, 2H, J=7.2 Hz); Anal. Calc. For C10H12S1O2: C, 61.22; H, 6.12. Found: C, 61.16; H, 6.28.

1. stirringstirred at room temperature for an additional 30 minutes
2. stirringthe resulting mixture was stirred
3. temperatureat reflux temperature for 6 hours
4. temperaturecooled to room temperature
5. concentrationconcentrated in vacuo
6. washThe residual solid was washed with 200 ml hexane/ether 2:1, v/v
7. stirringstirred for 15 minutes
8. filtrationThe solid was then filtered
9. washwashed with 100 ml hexane/ether
10. customdried under reduced pressure at room temperature

ORD record

ord-b3c126d8cf824959984c2b3a45acaec0

Source dataset

uspto-grants-2007_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07273880B2