Dimethyl Sulfoxide → 2-(Tert-Butylthio)Benzaldehyde

HRID 1681284Notes

Reaction equation

HRID 1681284 reaction equation
[OH-].[K+].[C:3]([SH:7])([CH3:6])([CH3:5])[CH3:4].CS(C)=O.Cl[C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH:15]=[O:16]>O.C(OCC)(=O)C>[CH3:4][C:3]([CH3:6])([S:7][C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH:15]=[O:16])[CH3:5]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6387tert-Butyl mercaptanHCID 69962-Chlorobenzaldehyde2×HCID 14797Potassium Hydroxide

Product 1

HCID 27769202-(Tert-Butylthio)Benzaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

Powdered potassium hydroxide (21.9 g, 390 mmol) and 56 ml (497 mmol) of terbutyl mercaptan were mixed 55.5 ml of dimethylsulfoxide in a 250 ml three-neck flask. To this stirred mixture was added dropwise over a ten minute period 50 g (356 mmol) of 2-chloro-benzaldehyde. During addition of the 2-chlorobenzaldehyde, the reaction mixture warmed to 120° C. After addition was complete, the mixture was allowed to react at about 110° C. for 1.5 hours. At the end of this time, the mixture was cooled to room temperature and taken up on 600 ml of ethyl acetate and 1 liter of water. The organic layer was separated, dried and evaporated to yield 2-(1,1-dimethylethylthio)benzaldehyde, b.p. 80°-82° C. at 0.05 mm Hg, which was used without further purification in the next step of the process.

Workup

  1. additionAfter addition
  2. customto react at about 110° C. for 1.5 hours
  3. temperatureAt the end of this time, the mixture was cooled to room temperature
  4. customThe organic layer was separated
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-499b8e0952bc4cb891027bfb4f45409b
Source dataset
uspto-grants-1992_12
Patent number
US05169961

Reaction notes

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