4-t-Amylbenzenesulphonyl chloride → 4-Pentylbenzene-1-thiol

Zinc dust (39 g) was added to a mixture of 4-n-pentylbenzenesulfonyl chloride (27 g, 0.11 ml) in concentrated sulfuric acid (43 ml) and water (270 ml) at less than 0° C. Thereafter, stirring was continued at a temperature less than 0° C. for about one hour followed by refluxing for approximately three hours. The reaction mixture was cooled and then poured into ice water (350 ml) and the reaction product was extracted with ether (2×400 ml). The extract was washed with water and dried over anhydrous sodium sulfate. The solvent (ether) was evaporated and the reaction product was vacuum-distilled to yield 4-n-pentylbenzenethiol (14 g, 71%, boiling point 90°-94° C./0.6 mm).

1. temperatureby refluxing for approximately three hours
2. temperatureThe reaction mixture was cooled
3. extractionthe reaction product was extracted with ether (2×400 ml)
4. washThe extract was washed with water
5. dry with materialdried over anhydrous sodium sulfate
6. customThe solvent (ether) was evaporated
7. distillationthe reaction product was vacuum-distilled

ORD record

ord-2bc34f9f9e49490fb2bb230f86daa7fa

Source dataset

uspto-grants-1984_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04424372