Thiophenol → 4-(Phenylsulfanyl)butan-1-ol

A mixture of thiophenol (121.2 g, 1.10 mole), 4-chloro-1-butanol (100.0 g, 0.921 mole), and potassium carbonate (138.2 g, 1.0 mole) was heated overnight at gentle reflux in dimethoxyethane. The reaction mixture was filtered and solvent removed by rotary evaporator. The residue obtained was dissolved in chloroform and extracted with 10% sodium hydroxide. The chloroform layer was dried, filtered, and solvent removed to give an oil which crystallized to a white solid. The solid was vacuum distilled at 134°-140° C./0.55 mm. A six-gram sample of the distilled oil was subjected to flash chromatography on silica gel using ethyl acetate-hexanes for elution. This gave a clear oil which was dried at 80° C. overnight in vacuo. The process produced 5.2 g (57.8%) of clear oil.

1. temperaturewas heated overnight
2. filtrationThe reaction mixture was filtered
3. customsolvent removed by rotary evaporator
4. customThe residue obtained
5. extractionextracted with 10% sodium hydroxide
6. dry with materialThe chloroform layer was dried
7. filtrationfiltered
8. customsolvent removed
9. customto give an oil which
10. customcrystallized to a white solid
11. distillationdistilled at 134°-140° C./0.55 mm
12. washfor elution
13. customThis gave a clear oil which
14. customwas dried at 80° C. overnight in vacuo

ORD record

ord-9b6bca417c434762bad8de93b51a34db

Source dataset

uspto-grants-1988_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04724235