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

HRID 240298

반응식

HRID 240298 반응식
[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]

참가 물질

6

반응물 4

HCID 65911,1,2,2-TetrachloroethaneHCID 7366Tert-ButylbenzeneHCID 7922Succinic anhydrideHCID 6451240Aluminum(III) Chloride2회

생성물 1

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

시약·촉매·용매 1

HCID 313Hydrochloric Acid용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-0447b6ba55d24bab9ef590255a74361a
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08648041B2

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