Hydrochloric Acid → 2-(2,4-Dichlorobenzoyl)cyclohexane-1,3-dione

HRID 1721826노트

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HRID 1721826 반응식
[C:1]1(=[O:8])[CH2:6][CH2:5][CH2:4][C:3](=[O:7])[CH2:2]1.[Cl:9][C:10]1[C:19](Cl)=[CH:18][CH:17]=[CH:16][C:11]=1[C:12](C#N)=[O:13].C(N(CC)CC)C.[ClH:28]>C(Cl)Cl.CCOCC.[Cl-].[Zn+2].[Cl-].C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Cl:9][C:10]1[CH:19]=[C:18]([Cl:28])[CH:17]=[CH:16][C:11]=1[C:12]([CH:2]1[C:3](=[O:7])[CH2:4][CH2:5][CH2:6][C:1]1=[O:8])=[O:13]

참가 물질

9

반응물 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 104341,3-CyclohexanedioneHCID 2735968(2,3-Dichlorophenyl)oxoacetonitrile

생성물 1

HCID 143016212-(2,4-Dichlorobenzoyl)cyclohexane-1,3-dione수율 77.7%

시약·촉매·용매 4

HCID 8895Cupric acetate촉매HCID 3007855Zincchloride촉매HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매

실험 절차

1,3-Cyclohexanedione [11.2 grams (g), 0.1 mole], 20.0 g (0.1 mole) 2,3-dichlorobenzoyl cyanide and 13.6 g (0.11 mole) anhydrous, powdered zinc chloride were combined in 100 milliliters (ml) methylene chloride. Triethylamine (10.1 g, 0.12 mole) was slowly added with cooling. The reaction mixture was stirred at room temperature for 5 hours and then poured into 2N hydrochloric acid. The aqueous phase was discarded and the organic phase was washed with 150 ml 5% Na2CO3 four times. The aqueous washings were combined and acidified with HCl, extracted with methylene chloride, dried and concentrated to yield 25.3 g of crude product. The crude product was dissolved in ether and stirred with 250 ml of 5% copper (II) acetate. The resulting copper salt was filtered, washed with ether and stirred with 6N hydrochloric acid to destroy the salt. The extract was washed with ether to yield 22.15 grams of the desired product m.p. 138°-140° C. (77.7% yield). The structure was confirmed by instrumental analysis.

후처리

  1. temperaturewith cooling
  2. washthe organic phase was washed with 150 ml 5% Na2CO3 four times
  3. extractionextracted with methylene chloride
  4. customdried
  5. concentrationconcentrated
  6. customto yield 25.3 g of crude product
  7. filtrationThe resulting copper salt was filtered
  8. washwashed with ether
  9. stirringstirred with 6N hydrochloric acid
  10. customto destroy the salt
  11. washThe extract was washed with ether

출처 및 근거

ORD 기록
ord-fbd621807d0a4340a9066728ad5d2069
출처 데이터셋
uspto-grants-1989_08
특허 번호
US04853028

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