Benzyl mercaptan → HCID 14111626, compound

HRID 1447046Notes

Reaction equation

HRID 1447046 reaction equation
[CH3:1][C:2]1(Cl)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[CH2:9]([SH:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[OH-:17].[Na+]>C(O)C>[CH3:1][C:2]1([S:16][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=[O:17]

Participants

5

Reactant 3

HCID 7509Benzyl mercaptanHCID 14798Sodium HydroxideHCID 1367321-Chloro-1-methylcyclohexane

Product 1

HCID 14111626HCID 14111626, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

36.5 g of 2-methyl-2-chlorocyclohexane are dissolved in 70 ml ethanol. To this solution is added a mixture of 82 g benzylmercaptan 26.4 g of sodium hydroxide and 330 ml ethanol and the whole is heated to reflux. A pink colour appears after 15 minutes and the mixture is then allowed to cool to room temperature and the solvent is distilled off. The oily residue is taken up in 400 ml water and the resulting suspension is extracted with methylene chloride. The organic phases are united, washed with water until neutral, dried over sodium sulphate and the solvent is evaporated off. The residue is purified by fractional distillation. 120 g of 2-methyl-2-benzylthiocyclohexanone are recovered, boiling at 142°-144° (yield=78%).

Workup

  1. additionTo this solution is added
  2. temperaturethe whole is heated to reflux
  3. distillationthe solvent is distilled off
  4. extractionthe resulting suspension is extracted with methylene chloride
  5. washwashed with water until neutral,
  6. dry with materialdried over sodium sulphate
  7. customthe solvent is evaporated off
  8. distillationThe residue is purified by fractional distillation
  9. custom120 g of 2-methyl-2-benzylthiocyclohexanone are recovered

Sources & evidence

ORD record
ord-a1590d37dbf24605b98fbcc53af33d39
Source dataset
uspto-grants-1982_02
Patent number
US04315031

Reaction notes

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