1,1,2,2-Tetrachloroethane → 4-(4-Tert-butylphenyl)-4-oxobutanoic acid

HRID 240298

反応式

HRID 240298 の反応式
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([CH3:8])([CH3:7])[CH3:6].[C:15]1(=[O:21])[O:20][C:18](=[O:19])[CH2:17][CH2:16]1.ClC(Cl)C(Cl)Cl>Cl>[C:5]([C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:21])[CH2:16][CH2:17][C:18]([OH:20])=[O:19])=[CH:11][CH:10]=1)([CH3:8])([CH3:7])[CH3:6]

参加物

6

反応物 4

HCID 65911,1,2,2-TetrachloroethaneHCID 7366Tert-ButylbenzeneHCID 7922Succinic anhydrideHCID 6451240Aluminum(III) Chloride2 回

生成物 1

HCID 20640374-(4-Tert-butylphenyl)-4-oxobutanoic acid

試薬・触媒・溶媒 1

HCID 313Hydrochloric Acid溶媒

実験手順

Aluminum chloride powder (80.0 g, 600 mmol) was added in portions to a stirred mixture of tert-butylbenzene (40.0 g, 300 mmol) and succinic anhydride (26.7 g, 267 mmol) and 1,1,2,2-tetrachloroethane (100 mL). After all the aluminum chloride had been added, the mixture was poured into a mixture of ice (500 mL) and concentrated hydrochloric acid (100 mL). The organic layer was separated, washed with water (500 mL) and the solvent distilled off. Solid residue was dissolved in hot 15% aqueous solution of sodium carbonate (1000 mL), filtered, cooled and the acid was precipitated with hydrochloric acid (acidified to pH=1). The crude acid was filtered, dried on air and recrystalised from benzene (500 mL) to give 4-(4-tert-butyl-phenyl)-4-oxo-butyric acid as colorless crystals.

後処理

  1. customThe organic layer was separated
  2. washwashed with water (500 mL)
  3. distillationthe solvent distilled off
  4. dissolutionSolid residue was dissolved in hot 15% aqueous solution of sodium carbonate (1000 mL)
  5. filtrationfiltered
  6. temperaturecooled
  7. customthe acid was precipitated with hydrochloric acid (acidified to pH=1)
  8. filtrationThe crude acid was filtered
  9. customdried on air
  10. customrecrystalised from benzene (500 mL)

出典と根拠

ORDレコード
ord-0447b6ba55d24bab9ef590255a74361a
出典データセット
uspto-grants-2014_02
特許番号
US08648041B2

関連ノート

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