Acetophenone → HCID 11858353, compound

HRID 1034536Notes

Reaction equation

HRID 1034536 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[C:10]([C:14]1[CH:22]=[CH:21][C:17]([C:18](Cl)=[O:19])=[CH:16][CH:15]=1)([CH3:13])([CH3:12])[CH3:11]>O>[C:10]([C:14]1[CH:15]=[CH:16][C:17]([C:18]([O:3][C:1]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[CH2:2])=[O:19])=[CH:21][CH:22]=1)([CH3:13])([CH3:11])[CH3:12]

Participants

4

Reactant 2

HCID 7410AcetophenoneHCID 743724-tert-Butylbenzoyl chloride

Product 1

HCID 11858353HCID 11858353, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4.16 g (21.62 mmol) of acetophenone trimethylsilylenol, 4.33 g (22.01 mmol) of 4-tert-butylbenzoyl chloride and 136 mg of mercuric chloride was heated at 100° C. for 2 h. The mixture was then left to cool, water was added over the reaction crude and extracted with dichloromethane. The organic phase was dried over magnesium sulfate and the solvent was removed under reduced pressure. A 2.12 g sample was purified by flash chromatography (hexane:dichloromethane 3:1) giving 1.17 g of 1-phenylvinyl 4-tert-butylbenzoate. Yield 57%.

Workup

  1. waitThe mixture was then left
  2. temperatureto cool
  3. extractionextracted with dichloromethane
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customA 2.12 g sample was purified by flash chromatography (hexane:dichloromethane 3:1)

Sources & evidence

ORD record
ord-ebb2d69525ac483c93f0a1552252adff
Source dataset
uspto-grants-2013_10
Patent number
US08545816B2

Reaction notes

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