Water → 2,5-Dimethoxythiophenol

HRID 1288611Notes

Reaction equation

HRID 1288611 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[S:11](Cl)(=O)=O.OS(O)(=O)=O.O.C(Cl)Cl>C1COCC1.[Zn]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[SH:11]

Participants

7

Reactant 4

HCID 962Water2×HCID 1118Sulfuric AcidHCID 6344DichloromethaneHCID 1370252,5-Dimethoxybenzenesulfonyl chloride

Product 1

HCID 5190092,5-Dimethoxythiophenol

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

16 g of 2,5-dimethoxybenzene-sulphonyl chloride are dissolved in 100 ml of THF, while stirring, and a mixture of 20 ml of concentrated H2SO4 and 60 ml of water is then added, followed by 25 g of zinc dust, added in portions at 50°-55° and stirring is continued overnight at 20°. The THF is then stripped off and the mixture is worked up with water and methylene chloride to give 2,5-dimethoxythiophenol, b.p. 106°-108°/0.3 mm.

Workup

  1. additionis then added
  2. additionadded in portions at 50°-55°
  3. stirringstirring

Sources & evidence

ORD record
ord-c9114d044c2d44d8b78390bc4b48f57f
Source dataset
uspto-grants-1976_10
Patent number
US03988468

Reaction notes

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