Potassium Carbonate → 2-(Cyclohexylthio)benzaldehyde

HRID 1919847Notes

Reaction equation

HRID 1919847 reaction equation
C([O-])([O-])=O.[K+].[K+].[CH:7]1([SH:13])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.F[C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1[CH:17]=[O:18]>CS(C)=O>[CH:7]1([S:13][C:15]2[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=2[CH:17]=[O:18])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 15290CyclohexanethiolHCID 67970o-Fluorobenzaldehyde

Product 1

HCID 638018692-(Cyclohexylthio)benzaldehydeYield 90.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred suspension of K2CO3 (4.5 g, 32.6 mmol) and cyclohexylmercaptan (2.0 mL, 16.4 mmol) in DMSO (20 mL) was added 2-fluorobenzaldehyde (1.7 mL, 16.2 mmol) dropwise over 10 minutes at room temperature, and the reaction mixture was heated at 100° C. for 5 hours with stirring. After cooling to room temperature, the reaction mixture was partitioned between ethyl acetate and water. The organic layer was separated and the aqueous phase extracted with ethyl acetate (×3). The combined organic extracts were washed successively with sodium bicarbonate solution and brine, then dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to afford 2-(cyclohexylthio)benzaldehyde (3.22 g, 14.6 mmol, 90%) which was used directly without further purification.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe reaction mixture was partitioned between ethyl acetate and water
  3. customThe organic layer was separated
  4. extractionthe aqueous phase extracted with ethyl acetate (×3)
  5. washThe combined organic extracts were washed successively with sodium bicarbonate solution and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-5c708c8361b04c53996b64ad4d118ec0
Source dataset
uspto-grants-2012_05
Patent number
US08168673B2

Reaction notes

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