Water → 4-Nitrobenzyl mercaptan

HRID 726417Notes

Reaction equation

HRID 726417 reaction equation
[S:1](=O)(=O)(O)O.O.C(O[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1)(=S)C.O>CO>[N+:18]([C:15]1[CH:16]=[CH:17][C:12]([CH2:11][SH:1])=[CH:13][CH:14]=1)([O-:20])=[O:19]

Participants

5

Reactant 3

HCID 962WaterHCID 197105064-Nitrobenzyl thioacetateHCID 21910475Sulfuric acid hydrate (1:1)

Product 1

HCID 1936194-Nitrobenzyl mercaptanYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Concentrated sulfuric acid--water (1:1 v/v; 17 cm3) was added to a stirred suspension of 4-nitrobenzyl thioacetate (8.0 g, 37.9 mmol) in methanol (150 cm3) and the reactants were heated, under reflux, for 3 h. The cooled products were poured into water (1.0 dm3) and the resulting mixture was extracted with diethyl ether (2×400 cm3). The combined organic extracts were washed with water (2×200 cm3), dried (MgSO4) and evaporated under reduced pressure to give 4-nitrobenzyl mercaptan 17a as a pale yellow solid (6.31 g, 98%).

Workup

  1. temperaturethe reactants were heated
  2. temperatureunder reflux, for 3 h
  3. extractionthe resulting mixture was extracted with diethyl ether (2×400 cm3)
  4. washThe combined organic extracts were washed with water (2×200 cm3)
  5. dry with materialdried (MgSO4)
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-c36e9c4fe94241b7809c243f93e7335b
Source dataset
uspto-grants-1998_01
Patent number
US05708161

Reaction notes

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