Thiophenol → 4-Tert-Butylbenzenethiol

HRID 1659506Notes

Reaction equation

HRID 1659506 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]C(C)(C)C)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C1(S)C=CC=CC=1>>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([SH:11])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 7969ThiophenolHCID 12801135HCID 12801135, compound

Product 1

HCID 754544-Tert-ButylbenzenethiolYield 129.6%

Conditions

Temperature
90 °C

Procedure

A mixture of 1285 grams (5.8 moles) of tert-butyl 4-(tert-butyl)phenyl sulfide (from replicates of EXAMPLE III) 1040 grams (9.5 moles) of thiophenol, and 350 grams of boron trifluoride-phosphoric acid complex was heated slowly to 90° C. The reaction mixture was stirred at 90° C. for four hours, cooled to 25° C., the organic layer was separated from the lower catalyst layer and added to 500 ml of toluene. This toluene solution was washed five times with 1000-ml portions of water, dried with magnesium sulfate, and then concentrated in vacuo. The residue was distilled through a 10-tray column to give 1250 grams (65% yield) of p-(tert-butyl)thiophenol, b.p. 58°-60°/1.0 mm. The nmr spectrum supported the proposed structure. A residue of 285 grams of 4-(tert-butyl)phenyl tert-butyl sulfide was obtained.

Workup

  1. temperaturecooled to 25° C.
  2. customthe organic layer was separated from the lower catalyst layer
  3. additionadded to 500 ml of toluene
  4. washThis toluene solution was washed five times with 1000-ml portions of water
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. distillationThe residue was distilled through a 10-tray column

Sources & evidence

ORD record
ord-1ca850d64a8848369fdeeb077ec6a668
Source dataset
uspto-grants-1981_12
Patent number
US04304735

Reaction notes

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