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

HRID 1764644

反応式

HRID 1764644 の反応式
[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

参加物

4

反応物 3

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

生成物 1

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

反応条件

温度
65 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-cab4969c458d4c51b0ed63328d8858ab
出典データセット
uspto-grants-1978_09
特許番号
US04117130

関連ノート

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