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

HRID 261091Notes

Reaction equation

HRID 261091 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]=O)=[CH:11][CH:10]=1)([CH3:7])[CH3:6])[CH3:2].[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:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][C:5]([CH3:7])([CH3:6])[C:4]([O:3][CH2:1][CH3:2])=[O:17])=[CH:10][CH:11]=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

In this manner 7.1 parts of ethyl(4-formylphenoxy)-2,2-dimethylacetate 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 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. Treatment of this ester with alcoholic potassium hydroxide for 2 hours, followed by extraction with ether, and acidification with dilute hydrochloric acid provides a precipitate which is 2-[4-(2-benzoylethenyl)phenoxy]-2,2-dimethylacetic acid.

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 ether
  5. customby evaporation at reduced pressure and column chromatography on silica gel

Sources & evidence

ORD record
ord-736a411ef10e4827bfef3addc31daf6f
Source dataset
uspto-grants-1979_08
Patent number
US04163859

Reaction notes

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