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

HRID 746269노트

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HRID 746269 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 1118Sulfuric Acid촉매HCID 176Acetic Acid용매

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온도
60 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d3b7260e801f42c58fc0bfd7af3da17e
출처 데이터셋
uspto-grants-1986_07
특허 번호
US04603201

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