Chlorobenzene → 4-(4-Chlorophenyl)-2-methyl-4-oxobutanoic acid

HRID 1764644

반응식

HRID 1764644 반응식
[CH3:1][CH:2]1[CH2:7][C:6](=[O:8])[O:5][C:3]1=[O:4].[Cl-].[Al+3].[Cl-].[Cl-].[Cl:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:6]([CH2:7][CH:2]([CH3:1])[C:3]([OH:5])=[O:4])=[O:8])=[CH:16][CH:15]=1

참가 물질

4

반응물 3

HCID 7964ChlorobenzeneHCID 20051Methylsuccinic anhydrideHCID 6451240Aluminum(III) Chloride

생성물 1

HCID 27337154-(4-Chlorophenyl)-2-methyl-4-oxobutanoic acid

반응 조건

온도
65 °C

실험 절차

To a solution of 114 g. of methylsuccinic anhydride in 400 ml. of chlorobenzene is added carefully 270 g. of aluminum chloride. The mixture is heated to 65° C. for 11/2 hours, is cooled, quenched with ice and concentrated hydrochloric acid and extracted with benzene. The benzene layer is extracted with aqueous sodium bicarbonate. After adjusting the pH of the bicarbonate solution to 6.3, concentrated hydrochloric acid is added slowly over a period of several hours with stirring. At pH 5.7, 78 g. of white crystals are filtered off. Recrystallization of this material from ethanol-water affords 3-(p-chlorobenzoyl)-2-methylpropionic acid as white crystals. A mixture of 35.50 g. of the preceding compound, 85 ml. of hydrazine hydrate and 400 ml. of ethyl alcohol is allowed to stir at reflux for 18 hours. The reaction mixture is concentrated to about 75% of the original volume, cooled in an ice bath and filtered to yield 26.62 g. of 6-(p-chlorophenyl)-4,5-dihydro-4-methyl-3(2H)-pyridazinone as a yellow solid. An additional 4.7 g. of product is obtained from the filtrate above.

후처리

  1. temperatureis cooled
  2. customquenched with ice and concentrated hydrochloric acid
  3. extractionextracted with benzene
  4. extractionThe benzene layer is extracted with aqueous sodium bicarbonate
  5. additionis added slowly over a period of several hours
  6. filtrationof white crystals are filtered off
  7. customRecrystallization of this material from ethanol-water

출처 및 근거

ORD 기록
ord-cab4969c458d4c51b0ed63328d8858ab
출처 데이터셋
uspto-grants-1978_09
특허 번호
US04117130

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