Potassium Carbonate → HCID 54309784, compound

HRID 376529Notes

Reaction equation

HRID 376529 reaction equation
Br[CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[CH2:8][CH:9]=[O:10].[CH3:11][O:12][C:13]1[CH:14]=[C:15]([SH:19])[CH:16]=[CH:17][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:11][O:12][C:13]1[CH:14]=[C:15]([S:19][CH:2]2[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]2[CH2:8][CH:9]=[O:10])[CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 849893-MethoxybenzenethiolHCID 54554648HCID 54554648, compound

Product 1

HCID 54309784HCID 54309784, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The mixture of 2-bromocyclohexylacetaldehyde 1.14 g, 3-methoxythiophenol 779 mg, potassium carbonate 1.54 g and acetone 20 ml is stirred at a room temperature for 21 hours. The solvent is distilled off under reduced pressure, and water 10 ml is added. Then, extraction is carried out twice with ethyl ether 20 ml. The organic layer is washed with saturated brine 5 ml and then dried on magnesium sulfate anhydrous. The solvent is distilled off under reduced pressure, and the residue is subjected to silica gel chromatography (hexane: chloroform=9:1), whereby colorless oily 2-(3-methoxyphenylthio)cyclohexylacetaldehyde 1.26 g is obtained. The yield: 86%.

Workup

  1. distillationThe solvent is distilled off under reduced pressure, and water 10 ml
  2. additionis added
  3. extractionThen, extraction
  4. washThe organic layer is washed with saturated brine 5 ml
  5. customdried on magnesium sulfate anhydrous
  6. distillationThe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-540d977cd5644a13b305b29d0329df6a
Source dataset
uspto-grants-2000_02
Patent number
US06020531

Reaction notes

Loading…