Propyl mercaptan → 4-Thiophen-2-ylphenol

HRID 1722749Notes

Reaction equation

HRID 1722749 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)=[CH:5][CH:4]=1.C(S)CC.[H-].[K+]>CN(C)C=O>[S:10]1[CH:11]=[CH:12][CH:13]=[C:9]1[C:6]1[CH:7]=[CH:8][C:3]([OH:2])=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 7848Propyl mercaptanHCID 82127Potassium hydrideHCID 27694252-(4-methoxyphenyl)thiophene

Product 1

HCID 35641974-Thiophen-2-ylphenol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 8.80 g (2-(4-methoxyphenyl)thiophene (prepared from 2-thienylmagnesium bromide and p-iodoanisole) and 5.4 ml propanethiol in 100 ml dry dimethylformamide was carefully added 7.00 g 35% potassium hydride in mineral oil. The reaction mixture was heated at reflux under nitrogen for 16 hours. Isolation of the resulting product afforded after crystallization 2.42 g 4-(2-thienyl)phenol as a yellow powder.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux under nitrogen for 16 hours
  3. customIsolation of the resulting product afforded
  4. customafter crystallization 2.42 g 4-(2-thienyl)phenol as a yellow powder

Sources & evidence

ORD record
ord-6af8107c215442038e8a7b4dff66d74b
Source dataset
uspto-grants-1989_08
Patent number
US04857539

Reaction notes

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