Methanethiol → 5-methyl-2-[1-methyl-1-(methylthio)ethyl]cyclohexan-1-one

HRID 1606268Notes

Reaction equation

HRID 1606268 reaction equation
[CH3:1][C@H:2]1[CH2:11][C:9](=[O:10])[C:5](=[C:6]([CH3:8])[CH3:7])[CH2:4][CH2:3]1.[CH3:12][SH:13]>C(N(CC)CC)C>[CH3:12][S:13][C:6]([CH3:7])([CH3:8])[CH:5]1[CH2:4][CH2:3][CH:2]([CH3:1])[CH2:11][C:9]1=[O:10]

Participants

4

Reactant 2

HCID 878MethanethiolHCID 442495(+)-Pulegone

Product 1

HCID 30204675-methyl-2-[1-methyl-1-(methylthio)ethyl]cyclohexan-1-one

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

15.2 g of pulegone are treated with 0.5 ml of triethylamine and cooled to ca 0° by means of an ice-common salt mixture. With stirring, methyl mercaptan in excess is condensed into the mixture and, after condensation of 200% of the calculated amount, the mixture is transferred into an autoclave. After standing overnight at room temperature, the reaction mixture is heated to 50° and, after cooling of the autoclave, the reaction product immediately distilled in vacuum. 9.8 g of 8-methylthio-p-menthan-3-one are obtained as a clear liquid with pleasant odour reminiscent of peppermint, geranium and caraway, boiling point 72°-73°/0.15 mm Hg, nD20 1.4982. The yield amounts to 73% of the theory based on reacted pulegone. The two stereoisomeric compounds 8-methylthio-cis-p-menthan-3-one and 8-methylthio-trans-p-menthan-3-one obtained can be separated gas-chromatographically.

Workup

  1. customcondensed into the mixture
  2. customafter condensation of 200% of the calculated amount
  3. temperaturethe reaction mixture is heated to 50°
  4. temperatureafter cooling of the autoclave
  5. distillationthe reaction product immediately distilled in vacuum

Sources & evidence

ORD record
ord-64f610ef36d34d01b493b04d0525f7dc
Source dataset
uspto-grants-1976_04
Patent number
US03952062

Reaction notes

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