Methanethiol → Methylmercapto-2-chlorocyclohexanone

HRID 2294766Notes

Reaction equation

HRID 2294766 reaction equation
[Cl:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=[O:8].[Na].[CH3:10][SH:11].O>C(O)C>[CH3:10][S:11][C:2]1([Cl:1])[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=[O:8]

Participants

6

Reactant 4

HCID 878MethanethiolHCID 962WaterHCID 132032-ChlorocyclohexanoneHCID 5360545Sodium

Product 1

HCID 54407380Methylmercapto-2-chlorocyclohexanoneYield 78%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a 300-ml egg-plant type flask 7.07 g (0.053 mol) of 2-chlorocyclohexanone was dissolved in 50 ml of ethanol, and 25 ml of 15% aqueous solution of sodium salt of methylmercaptan was added dropwise with a dropping funnel, and the mixture was stirred at room temperature for 3 h. The reaction mixture was poured into 300 ml of water, and an organic layer was extracted with methylene chloride, dried with magnesium sulfate and distilled to remove methylene chloride. After that reduced pressure distillation was performed to obtain 6.0 g of methylmercapto-2-chlorocyclohexanone (78% yield; b.p. 48.5°-47.5° C./0.3 mmHg).

Workup

  1. extractionan organic layer was extracted with methylene chloride
  2. dry with materialdried with magnesium sulfate
  3. distillationdistilled
  4. customto remove methylene chloride
  5. distillationAfter that reduced pressure distillation

Sources & evidence

ORD record
ord-009bcf70564a4317818b21a0e11ac4a2
Source dataset
uspto-grants-1997_11
Patent number
US05691111

Reaction notes

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