Thiophenol → Benzene, ((1,1-dimethylethyl)thio)-

HRID 1659504Notes

Reaction equation

HRID 1659504 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:8][C:9](=[CH2:11])[CH3:10]>>[C:1]1([S:7][C:9]([CH3:11])([CH3:10])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 7969ThiophenolHCID 8255Isobutylene

Product 1

HCID 137798Benzene, ((1,1-dimethylethyl)thio)-Yield 94%

Procedure

To a mixture of 55 grams (0.5 mole) of thiophenol and 51 grams of boron trifluoride-phosphoric acid complex was slowly added, with stirring and cooling, 34 grams (0.6 mole) of isobutylene at 0° C. After addition was complete the mixture was stirred at 0° C. for two hours. The organic layer was separated from the catalyst layer and added to 200 ml of toluene. The toluene layer was distilled in a one-foot packed column to give 78 grams of tert-Butyl Phenyl Sulfide, b.p. 55°/3.0 mm (yield 94%). The nmr spectrum agreed with the proposed structure.

Workup

  1. additionwas slowly added
  2. temperaturecooling
  3. customat 0° C
  4. additionAfter addition
  5. stirringwas stirred at 0° C. for two hours
  6. customThe organic layer was separated from the catalyst layer
  7. additionadded to 200 ml of toluene
  8. distillationThe toluene layer was distilled in a one-foot

Sources & evidence

ORD record
ord-ecb668ea7e35434eada40df1bf936678
Source dataset
uspto-grants-1981_12
Patent number
US04304735

Reaction notes

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