Sodium Hydroxide → 2-tert-butylbenzenethiol

HRID 1708510Notes

Reaction equation

HRID 1708510 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11]CN(C)C(=O)[O-])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[SH:11])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86748200HCID 86748200, compound

Product 1

HCID 27950322-tert-butylbenzenethiolYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a well stirred solution of the carbamate (30.0 g, 0.127 mol) dissolved in 500 ml of methanol was added a solution of sodium hydroxide (15.2 g, 0.38 mol) in methanol (100 ml). The resulting mixture was stirred at room temperature for 30 min followed by gentle reflux (1.5 h) to completion (TLC). Usual work-up followed by flash chromatography yielded 2-tert-butylbenzenethiol (18.0 g, 86% yield) as a pale yellow liquid.

Workup

  1. temperatureby gentle reflux (1.5 h) to completion (TLC)

Sources & evidence

ORD record
ord-05dd0d0f8d95439694c25cba94b065dc
Source dataset
uspto-grants-1994_10
Patent number
US05359065

Reaction notes

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