Methanethiol → 2-Butanone, 3,3-dimethyl-1-(methylthio)-

HRID 262362Notes

Reaction equation

HRID 262362 reaction equation
[O-]CC.[Na+].[Na].[CH3:6][SH:7].C[S-].Br[CH2:11][C:12](=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14]>>[CH3:14][C:13]([CH3:16])([CH3:15])[C:12](=[O:17])[CH2:11][S:7][CH3:6]

Participants

6

Reactant 5

HCID 878MethanethiolHCID 21642BromopinacoloneHCID 519392MercaptomethanideHCID 2723922Sodium ethoxideHCID 5360545Sodium

Product 1

HCID 1701682-Butanone, 3,3-dimethyl-1-(methylthio)-

Procedure

To a solution of sodium ethoxide prepared from 7.7 g (0.33 mol) of sodium metal and 200 ml of absolute alcohol was added 19 g (0.4 mol) of methanethiol over 10 min at ±2° C. To this solution of thiomethoxide was added dropwise, over 25 min. 59 g (0.28 mol) of 1-bromo-3,3-dimethyl-2-butanone prepared according to the procedure of J. Am. Chem. Soc. 74, 4507 (1952). The temperature was maintained at 0°±3° C. during the addition and for a further 30 min. The reaction mixture was filtered and the solvent removed by distillation. Vacuum distillation of the residue gave the desired product as a colorless liquid, b. 73° C./9.3 mm Hg, nD24 1.4650 in 54% pure yield.

Workup

  1. temperatureThe temperature was maintained at 0°±3° C. during the addition and for a further 30 min
  2. filtrationThe reaction mixture was filtered
  3. customthe solvent removed by distillation
  4. distillationVacuum distillation of the residue

Sources & evidence

ORD record
ord-cb3acaf0ea4744abab730bdc2f47f07f
Source dataset
uspto-grants-1979_05
Patent number
US04154732

Reaction notes

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