4'-Methoxyacetophenone → Methyl 4-methoxy-beta-oxobenzenepropanoate

HRID 1590543

反応式

HRID 1590543 の反応式
[Na].[C:2](=[O:7])([O:5][CH3:6])OC.[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16](=[O:18])[CH3:17])=[CH:12][CH:11]=1>C1(C)C=CC=CC=1>[O:18]=[C:16]([C:13]1[CH:14]=[CH:15][C:10]([O:9][CH3:8])=[CH:11][CH:12]=1)[CH2:17][C:2]([O:5][CH3:6])=[O:7]

参加物

5

反応物 3

HCID 74764'-MethoxyacetophenoneHCID 12021Dimethyl CarbonateHCID 5360545Sodium

生成物 1

HCID 2759699Methyl 4-methoxy-beta-oxobenzenepropanoate

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒3 回

反応条件

温度
93 °C

実験手順

30.7 g of sodium was added to 300 ml of toluene, and the mixture was heated to 93° C., followed by cooling while vigorous stirring, to give sandy products. To the product, 600 ml of toluene containing 300 g of dimethyl carbonate was added, and further 250 ml of a toluene solution containing 100 g of p-methoxyacetophenone was added dropwise over 2 hours and 15 minutes at 84° to 86° C. After the dropwise addition, the mixture was stirred under heating at 82° to 83° C. for 1.5 hours, and then the solvent was evaporated. To the residue was added 1 l of isopropyl ether, and crystals were collected by filtration and washed with 500 ml of isopropyl ether. These crystals were added to a mixture of ice and ethyl acetate containing 100 g of acetic acid, and extracted with ethyl acetate. The extract was washed with 5 % sodium hydrogen carbonate and then with water, and dried. Subsequently, the solvent was evaporated to obtain 131.6 g of methyl 3-oxo-3-(p-methoxyphenyl)propionate as an oily product.

後処理

  1. temperatureby cooling while vigorous stirring
  2. customto give sandy products
  3. additionwas added dropwise over 2 hours and 15 minutes at 84° to 86° C
  4. additionAfter the dropwise addition
  5. temperatureunder heating at 82° to 83° C. for 1.5 hours
  6. customthe solvent was evaporated
  7. additionTo the residue was added 1 l of isopropyl ether, and crystals
  8. filtrationwere collected by filtration
  9. washwashed with 500 ml of isopropyl ether
  10. additionThese crystals were added to a mixture of ice and ethyl acetate containing 100 g of acetic acid
  11. extractionextracted with ethyl acetate
  12. washThe extract was washed with 5 % sodium hydrogen carbonate
  13. dry with materialwith water, and dried
  14. customSubsequently, the solvent was evaporated

出典と根拠

ORDレコード
ord-183ea84382d044d3a6b812e2768cbbf3
出典データセット
uspto-grants-1993_04
特許番号
US05204248

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