Methanethiol → Carvone, (+-)-

HRID 1605611Notes

Reaction equation

HRID 1605611 reaction equation
[CH3:1][C:2]1[C:7](=[O:8])[CH2:6][CH:5]([C:9]([CH3:11])=[CH2:10])[CH2:4][CH:3]=1.[CH3:12][SH:13]>C(N(CC)CC)C>[CH3:1][C:2]1[C:7](=[O:8])[CH2:6][CH:5]([C:9]([CH3:11])=[CH2:10])[CH2:4][CH:3]=1.[CH3:12][S:13][CH:3]1[CH:2]([CH3:1])[C:7](=[O:8])[CH2:6][CH:5]([C:9]([CH3:11])=[CH2:10])[CH2:4]1

Participants

5

Reactant 2

HCID 878MethanethiolHCID 7439Carvone, (+-)-

Product 2

HCID 7439Carvone, (+-)-HCID 1228992-Methyl-5-(1-methylthio)-3-(methylvinyl)cyclohexan-1-one

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
50 °C

Procedure

15.0 g of carvone are mixed with 0.5 g of triethylamine. 20 ml of methyl mercaptan are condensed in this mixture at room temperature. After standing overnight in the autoclave, the mixture is heated to 50° C for a further 2 hours. After removal of the excess methyl mercaptan, the reaction product is fractionally distilled in vacuum. After a small fore-run of unreacted carvone, there are obtained 14.9 g of 6-methylthio-p-menth-8-en-2-one in the form of a mixture of two isomers in the ratio 1:4 (boiling point 105°-107°/0.2 mm Hg, nD20 1.5067), corresponding to a yield of 78% of the theory. The odour of the mixture is reminiscent of boiled white cabbage with a caraway and onion peel note.

Workup

  1. customcondensed in this mixture at room temperature
  2. customAfter removal of the excess methyl mercaptan
  3. distillationthe reaction product is fractionally distilled in vacuum

Sources & evidence

ORD record
ord-8511e5b462944237be7228c8a88b8e24
Source dataset
uspto-grants-1976_04
Patent number
US03950429

Reaction notes

Loading…