Diisopropyl Ether → 4-(3,5-Dichloro-4-methylphenyl)-4-oxobut-2-enoic acid

HRID 746269ノート

反応式

HRID 746269 の反応式
C([O:4][C:5](=[O:7])[CH3:6])(=O)C.O.C(O)(=O)C=O.[CH3:14][C:15]1[C:20]([Cl:21])=[CH:19][C:18]([C:22]([CH3:24])=[O:23])=[CH:17][C:16]=1[Cl:25].C(OC(C)C)(C)C>S(=O)(=O)(O)O.C(O)(=O)C>[Cl:21][C:20]1[CH:19]=[C:18]([C:22](=[O:23])[CH:24]=[CH:6][C:5]([OH:4])=[O:7])[CH:17]=[C:16]([Cl:25])[C:15]=1[CH3:14]

参加物

7

反応物 4

HCID 7914Diisopropyl EtherHCID 7918Acetic AnhydrideHCID 137135291-(3,5-Dichloro-4-methylphenyl)ethan-1-oneHCID 15620607Glyoxylic acid, monohydrate

生成物 1

HCID 545341534-(3,5-Dichloro-4-methylphenyl)-4-oxobut-2-enoic acid収率 80.3%

試薬・触媒・溶媒 2

HCID 1118Sulfuric Acid触媒HCID 176Acetic Acid溶媒

反応条件

温度
60 °C

実験手順

10.2 g (0.1 mole) of acetic anhydride were added to 9.3 g (0.1 mole) of glyoxylic acid monohydrate and the mixture was heated, with stirring, on an oil bath at 60° C. for 10 minutes to obtain a homogeneous solution. To this solution were added, in turn, 20.3 g (0.1 mole) of 3,5-dichloro-4-methylacetophenone, prepared as described in step (a) above, 28.8 g of acetic acid and a catalytic amount (300 mg) of concentrated sulphuric acid, whilst ice-cooling. The mixture was then heated, with stirring, on an oil bath at 105°-110° C. for 2 hours, after which it was cooled and 100 ml of diisopropyl ether were added. The mixture was stirred and the resulting crystals were collected by filtration and washed first with water and then with a small amount of diisopropyl ether, after which they were dried to give 20.8 g (yield 80.3%) of the desired 4-(3,5-dichloro-4-methylphenyl)-4-oxo-2-butenoic acid, melting at 206°-216° C.

後処理

  1. temperaturethe mixture was heated
  2. customto obtain a homogeneous solution
  3. customprepared
  4. temperatureThe mixture was then heated
  5. stirringwith stirring, on an oil bath at 105°-110° C. for 2 hours
  6. temperatureafter which it was cooled
  7. stirringThe mixture was stirred
  8. filtrationthe resulting crystals were collected by filtration
  9. washwashed first with water
  10. dry with materialwith a small amount of diisopropyl ether, after which they were dried

出典と根拠

ORDレコード
ord-d3b7260e801f42c58fc0bfd7af3da17e
出典データセット
uspto-grants-1986_07
特許番号
US04603201

反応ノート

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