Methanol → 4-Chloro-4'-ethylthiomethylbenzophenone

HRID 1421545Notes

Reaction equation

HRID 1421545 reaction equation
[Br-].[Cl:2][C:3]1[CH:21]=[CH:20][C:6]([C:7]([C:9]2[CH:19]=[CH:18][C:12]([CH2:13][S:14][C:15](N)=[NH2+])=[CH:11][CH:10]=2)=[O:8])=[CH:5][CH:4]=1.[C:22](=O)([O-])[O-].[K+].[K+].CO.[OH-].[K+]>C1(C)C=CC=CC=1.O>[Cl:2][C:3]1[CH:21]=[CH:20][C:6]([C:7]([C:9]2[CH:19]=[CH:18][C:12]([CH2:13][S:14][CH2:15][CH3:22])=[CH:11][CH:10]=2)=[O:8])=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 18779877S-(4-(4-chlorobenzoyl)benzyl)thiouronium bromide

Product 1

HCID 196893544-Chloro-4'-ethylthiomethylbenzophenoneYield 52.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

S-(4-(4-chlorobenzoyl)benzyl)thiouronium bromide (3.3 g) and potassium carbonate (1.5 g) were dissolved in dimethylformnamide (20 ml). A methanol solution (10 ml) of potassium hydroxide (1.0 g) was added and stirred at room temperature for 30 minutes. To the reaction mixture, water (100 ml) and toluene (100 ml) were added. The organic layer was separated, and washed with water and an aqueous saturated sodium chloride solution, followed by drying over anhydrous magnesium sulfate. After distilling off the solvent, the crude product was purified by silica gel column chromatography (developing solvent: ethyl acetaten:hexane=1:9) to obtain 4-chloro-4'-ethylmercaptomethylbenzophenone (1.3 g).

Workup

  1. customThe organic layer was separated
  2. washwashed with water
  3. dry with materialby drying over anhydrous magnesium sulfate
  4. distillationAfter distilling off the solvent
  5. customthe crude product was purified by silica gel column chromatography (

Sources & evidence

ORD record
ord-54e40a5d942344f9a6b07f05d96c6218
Source dataset
uspto-grants-2000_06
Patent number
US06077866

Reaction notes

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