Hydrochloric Acid → alpha-(4-Tert-butylphenyl)-beta-hydroxy-beta-(2-trifluoromethylphenyl)acrylonitrile

HRID 1168414

반응식

HRID 1168414 반응식
[H-].[Na+].[C:3]([C:7]1[CH:15]=[CH:14][C:10]([CH2:11][C:12]#[N:13])=[CH:9][CH:8]=1)([CH3:6])([CH3:5])[CH3:4].[F:16][C:17]([F:28])([F:27])[C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20](Cl)=[O:21].Cl>CCCCCC.O.O1CCCC1>[C:3]([C:7]1[CH:8]=[CH:9][C:10]([C:11](=[C:20]([OH:21])[C:19]2[CH:23]=[CH:24][CH:25]=[CH:26][C:18]=2[C:17]([F:16])([F:27])[F:28])[C:12]#[N:13])=[CH:14][CH:15]=1)([CH3:6])([CH3:4])[CH3:5]

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 675612-(Trifluoromethyl)benzoyl chlorideHCID 76784(4-tert-Butylphenyl)acetonitrile

생성물 1

HCID 70026415alpha-(4-Tert-butylphenyl)-beta-hydroxy-beta-(2-trifluoromethylphenyl)acrylonitrile수율 95.8%

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

실험 절차

A mixture comprising 5.8 g of 63% sodium hydride, 25 ml of tetrahydrofuran and 10 ml of liquid paraffin, was heated, and a mixture comprising 13.5 g of 4-tert-butylbenzyl cyanide and 15.0 g of 2-trifluoromethylbenzoyl chloride, was dropwise added thereto over a period of 2 hours at a temperature of from 65 to 70° C. After completion of the dropwise addition, the reaction was carried out for 2 hours at the same temperature. The reaction mixture was left to cool to room temperature, and 250 ml of water was poured into the solution. Then, 80 ml of n-hexane was poured, followed by stirring and washing for 10 minutes, and the mixture was left to stand still for 30 minutes, whereupon the aqueous layer was separated and obtained. To the aqueous layer, 8.3 g of concentrated hydrochloric acid was gradually dropwise added with stirring, followed by further stirring for 30 minutes. Precipitated crystals were collected by filtration and washed with 100 ml of water, and then dried at 55° C. for 24 hours to obtain 23.8 g of the desired product. The NMR spectrum data of this product were the same as in Reference Preparation Example 1.

후처리

  1. temperaturewas heated
  2. additionAfter completion of the dropwise addition
  3. waitthe reaction was carried out for 2 hours at the same temperature
  4. waitThe reaction mixture was left
  5. washwashing for 10 minutes
  6. waitthe mixture was left
  7. waitto stand still for 30 minutes, whereupon the aqueous layer
  8. customwas separated
  9. customobtained
  10. stirringwith stirring
  11. stirringby further stirring for 30 minutes
  12. customPrecipitated crystals
  13. filtrationwere collected by filtration
  14. washwashed with 100 ml of water
  15. customdried at 55° C. for 24 hours

출처 및 근거

ORD 기록
ord-f5698ed9125142b3a59b39212dabd4d9
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06624179B1

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