Hydrochloric Acid → 3,4,5-Trimethoxy(4,4-dimethyl-3-oxopentanoyl)benzene

HRID 1613005노트

반응식

HRID 1613005 반응식
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([O:17][CH3:18])[C:14]=1[O:15][CH3:16])[C:8]([O:10]C)=O.[CH3:19][C:20](=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22].Cl>CCCCCC.O1CCCC1>[CH3:18][O:17][C:13]1[CH:12]=[C:7]([C:8](=[O:10])[CH2:19][C:20](=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22])[CH:6]=[C:5]([O:4][CH3:3])[C:14]=1[O:15][CH3:16]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 6416PinacoloneHCID 15956Methyl 3,4,5-trimethoxybenzoateHCID 24758Sodium hydride

생성물 1

HCID 197775673,4,5-Trimethoxy(4,4-dimethyl-3-oxopentanoyl)benzene수율 74%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

실험 절차

In a 200 ml three-necked flask equipped with a mechanical stirrer, dropping funnel, reflux condenser, and a nitogen-inlet tube, 3.0 gm (75 mmol) of 60% sodium hydride, 10 gm (44.3 mmol) of methyl 3,4,5-trimethoxybenzoate, and 80 ml of anhydrous tetrahydrofuran were mixed with stirring under nitrogen stream, and refluxed with heating while 5.3 gm (53.2 mmol) of pinacolone was added dropwise. Refluxing under heat was continued for 5 hours. After cooling the reaction mixture, 45 ml of 2N hydrochloric acid was added, the mixture was extracted twice with chloroform. The extract was dried over anhydrous sodium sulfate and the solvent was removed by evaporation to give a crude product. Hexane was added to the crude product and insoluble substances were filtered off. The filtrate was concentrated by evaporation, and recrystallization afforded 9.6 gm of the target compound as colorless needles (yield: 74%).

후처리

  1. customIn a 200 ml three-necked flask equipped with a mechanical stirrer
  2. temperaturereflux condenser, and a nitogen-inlet tube
  3. temperaturerefluxed
  4. additionwas added dropwise
  5. temperatureRefluxing
  6. temperatureunder heat
  7. additionwas added
  8. extractionthe mixture was extracted twice with chloroform
  9. dry with materialThe extract was dried over anhydrous sodium sulfate
  10. customthe solvent was removed by evaporation
  11. customto give a crude product
  12. filtrationwere filtered off
  13. concentrationThe filtrate was concentrated by evaporation, and recrystallization

출처 및 근거

ORD 기록
ord-af23f4b663924bea9becb7e5ce01a7ac
출처 데이터셋
uspto-grants-1993_03
특허 번호
US05191121

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