Acetophenone → Ethyl 2-[4-(2-benzoylethenyl)phenoxy]-2,2-dimethylacetate

HRID 261092Notes

Reaction equation

HRID 261092 reaction equation
[CH:1]([C:3]1[CH:17]=[CH:16][C:6]([O:7][C:8]([CH3:15])([CH3:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:5][CH:4]=1)=O.[C:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:20])[CH3:19]>C(O)C>[C:18]([CH:19]=[CH:1][C:3]1[CH:17]=[CH:16][C:6]([O:7][C:8]([CH3:15])([CH3:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:5][CH:4]=1)(=[O:20])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 7410AcetophenoneHCID 13134808Ethyl 2-(4-formylphenoxy)-2-methylpropanoate

Product 1

HCID 53866496Ethyl 2-[4-(2-benzoylethenyl)phenoxy]-2,2-dimethylacetate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

7.1 Parts of ethyl (4-formylphenoxy)-2,2-dimethylacetate described in U.S. Pat. No. 3,842,120 and 4.7 parts of acetophenone in 10 parts by volume of ethanol containing 0.01 part of sodium ethyl are reacted for 2 hours. This reaction mixture is quenched with 100 parts of cold water and extracted with ether. The ether extracts are dried over magnesium sulfate. Filtration of the magnesium sulfate, removal of the ether by evaporation at reduced pressure, and column chromatography on silica gel provides ethyl 2-[4-(2-benzoylethenyl)phenoxy]-2,2-dimethylacetate, melting at 68° to 70° C. This compound has the following structural formula ##STR5##

Workup

  1. customThis reaction mixture is quenched with 100 parts of cold water
  2. extractionextracted with ether
  3. dry with materialThe ether extracts are dried over magnesium sulfate
  4. filtrationFiltration of the magnesium sulfate, removal of the ether
  5. customby evaporation at reduced pressure, and column chromatography on silica gel

Sources & evidence

ORD record
ord-509fb81b846743eda63fe18983246945
Source dataset
uspto-grants-1979_08
Patent number
US04163859

Reaction notes

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