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Ethylene Glycol → 2-Isopropyl-7-(4'-tert-butylphenyl)-1-indanone

HRID 1392351
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인쇄 미리보기

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HRID 1392351 반응식
[CH:1]([CH:4]1[CH2:12][C:11]2[C:6](=[C:7](Cl)[CH:8]=[CH:9][CH:10]=2)[C:5]1=[O:14])([CH3:3])[CH3:2].[C:15]([C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1)([CH3:18])([CH3:17])[CH3:16].C(=O)([O-])[O-].[Na+].[Na+].C(O)CO>O>[CH:1]([CH:4]1[CH2:12][C:11]2[C:6](=[C:7]([C:22]3[CH:23]=[CH:24][C:19]([C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:20][CH:21]=3)[CH:8]=[CH:9][CH:10]=2)[C:5]1=[O:14])([CH3:3])[CH3:2]
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참가 물질

6

반응물 4

HCID 174Ethylene GlycolHCID 10340Sodium CarbonateHCID 27343204-tert-Butylphenylboronic acidHCID 221729527-Chloro-2,3-dihydro-2-(1-methylethyl)-1H-inden-1-one

생성물 1

HCID 231055462-Isopropyl-7-(4'-tert-butylphenyl)-1-indanone수율 97.3%

시약·촉매·용매 1

HCID 962
Water
용매
2회

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온도
80 °C

실험 절차

28.0 g of 2-isopropyl-7-chloro-1-indanone, 28.64 g of 4-tert-butylphenylboronic acid, 35.56 g of sodium carbonate, 302 ml of ethylene glycol and 21.6 ml of water are placed in a reaction vessel. The mixture is degassed a number of times by careful application of an oil pump vacuum and subsequent admission of argon, and thus saturated with argon. It is heated to 80° C. and a freshly prepared catalyst solution comprising 60.23 mg of palladium acetate and 1.79 ml of an aqueous TPPTS solution (0.6 molar) in 25 ml of water is then added while stirring vigorously and the reaction mixture is refluxed for 5 hours with further stirring until completely reacted. After cooling to room temperature, 300 ml of water are added. After renewed cooling to room temperature, the ethylene glycol phase is washed 6 times with a total of 900 ml of toluene. The combined toluene phases are washed twice with a total of 250 ml of sodium chloride solution and dried over 150 g of sodium sulfate. Removal of the solvent on a rotary evaporator, drying of the residue and subsequent distillation in an oil pump vacuum gives 40 g (97%) of 2-isopropyl-7-(4′-tert-butylphenyl)-1-indanone as an orange-brown, viscous oil.

후처리

  1. customThe mixture is degassed a number of times by careful application of an oil pump vacuum and subsequent admission of argon
  2. additionis then added
  3. temperaturethe reaction mixture is refluxed for 5 hours
  4. stirringwith further stirring
  5. customuntil completely reacted
  6. temperatureAfter cooling to room temperature
  7. temperatureAfter renewed cooling to room temperature
  8. washthe ethylene glycol phase is washed 6 times with a total of 900 ml of toluene
  9. washThe combined toluene phases are washed twice with a total of 250 ml of sodium chloride solution
  10. dry with materialdried over 150 g of sodium sulfate
  11. customRemoval of the solvent
  12. customon a rotary evaporator
  13. customdrying of the residue and subsequent distillation in an oil pump vacuum

출처 및 근거

ORD 기록
ord-1161eb7b533145549cd03fc931a524f2
출처 데이터셋
uspto-grants-2008_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07342078B2

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