Benzene → Chloromethyl phenyl sulphide

Temperature

31 °C

With stirring, 37.5 grams (1.25 moles) of paraformaldehyde was added to 250 ml of benzene. To the benzene-paraformaldehyde mixture 500 ml of concentrated hydrochloric acid was added slowly at ambient temperature. The mixture was then heated at 31° C. for 30 minutes, and 110 grams of thiophenol was added. Upon complete addition the reaction mixture was heated at 50°-55° C. for 2 hours, then allowed to cool to ambient temperature where it stood for 18 hours. The reaction mixture was separated and the organic layer washed with 250 ml of water. The water wash was extracted with 250 ml of benzene and the two benzene layers were combined. The benzene combination was washed with 300 ml of aqueous saturated sodium chloride, dried with magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure to a residue which was further evaporated under high vacuum and distilled to give 115.9 grams (73.2%) of phenylthiomethyl chloride; b.p. 80° C./3 mm. The nmr and the ir spectra were consistent with the assigned structure.

1. additionUpon complete addition the reaction mixture
2. temperaturewas heated at 50°-55° C. for 2 hours
3. temperatureto cool to ambient temperature where it
4. customThe reaction mixture was separated
5. washthe organic layer washed with 250 ml of water
6. washThe water wash
7. extractionwas extracted with 250 ml of benzene
8. washThe benzene combination was washed with 300 ml of aqueous saturated sodium chloride
9. dry with materialdried with magnesium sulfate
10. filtrationfiltered
11. customThe filtrate was evaporated under reduced pressure to a residue which
12. customwas further evaporated under high vacuum
13. distillationdistilled

ORD record

ord-23b49e46f2eb4f318ace7fca5bc8e063

Source dataset

uspto-grants-1980_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04215069