Potassium Hydroxide → 3-Methoxy-5-methylbenzenethiol

HRID 422129Notes

Reaction equation

HRID 422129 reaction equation
CN(C)C(=O)[S:4][C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([O:12][CH3:13])[CH:6]=1.[OH-].[K+]>CO>[CH3:13][O:12][C:7]1[CH:6]=[C:5]([SH:4])[CH:10]=[C:9]([CH3:11])[CH:8]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 58294823S-3-methoxy-5-methylphenyl dimethylcarbamothioate

Product 1

HCID 225047193-Methoxy-5-methylbenzenethiolYield 99.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of S-3-methoxy-5-methylphenyl dimethylcarbamothioate (10) (4.10 g, 18.2 mmol) and KOH (6.0 g) in MeOH (200 mL) was refluxed for 2 h. After cooling, the mixture was concentrated and diluted with EtOAc (500 mL). The organics were washed with 1N HCl (50 mL), brine (2×50 mL), dried (Na2SO4), and concentrated to give 3-methoxy-5-methylbenzenethiol (11) (2.80 g, quant.) as a colourless oil.

Workup

  1. temperaturewas refluxed for 2 h
  2. temperatureAfter cooling
  3. concentrationthe mixture was concentrated
  4. additiondiluted with EtOAc (500 mL)
  5. washThe organics were washed with 1N HCl (50 mL), brine (2×50 mL)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8683a2fbae034731a20ad5db5adbfc84
Source dataset
uspto-grants-2012_01
Patent number
US08101605B2

Reaction notes

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