2,3-Dimethylanisole → 2,2-Diethyl-4,5-dimethyl-6-methoxy-indan-1,3-dione

HRID 1659171

반응식

HRID 1659171 반응식
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[O:9][CH3:10].[CH2:11]([C:13]([CH2:20][CH3:21])([C:17](Cl)=[O:18])[C:14](Cl)=[O:15])[CH3:12].[Cl-].[Al+3].[Cl-].[Cl-]>CCCCCC>[CH2:11]([C:13]1([CH2:20][CH3:21])[C:14](=[O:15])[C:6]2[C:5](=[CH:4][C:3]([O:9][CH3:10])=[C:2]([CH3:1])[C:7]=2[CH3:8])[C:17]1=[O:18])[CH3:12]

참가 물질

5

반응물 3

HCID 762692,3-DimethylanisoleHCID 4149059Diethylmalonyl dichlorideHCID 6451240Aluminum(III) Chloride

생성물 1

HCID 215167892,2-Diethyl-4,5-dimethyl-6-methoxy-indan-1,3-dione

시약·촉매·용매 1

HCID 8058Hexane용매

반응 조건

온도
0 °C

실험 절차

A stirred mixture of 2,3-dimethylanisole (6.8 g., 0.05 mole) and 2,2-diethylmalonyl chloride (10 g., 0.051 mole) in hexane (75ml.) is cooled to 0°C. and treated with aluminum chloride (13.5 g., 0.11 mole) in several portions over a 15 minute period. The reaction is heated at reflux for 2 hours, the hexane is distilled at reduced pressure, the product treated with cold 1N-hydrochloric acid, extracted into ether, washed with water, 5% sodium hydroxide, water then dried over magnesium sulfate. Evaporation of the ether at reduced pressure affords 6.3 g. of 2,2-diethyl-4,5-dimethyl-6-methoxy-indan-1,3-dione which melts at 80°-81°C. after recrystallization from petroleum ether.

후처리

  1. temperatureThe reaction is heated
  2. temperatureat reflux for 2 hours
  3. distillationthe hexane is distilled at reduced pressure
  4. additionthe product treated with cold 1N-hydrochloric acid
  5. extractionextracted into ether
  6. washwashed with water, 5% sodium hydroxide, water
  7. dry with materialthen dried over magnesium sulfate
  8. customEvaporation of the ether at reduced pressure
  9. customaffords 6.3 g
  10. customof 2,2-diethyl-4,5-dimethyl-6-methoxy-indan-1,3-dione which melts at 80°-81°C. after recrystallization from petroleum ether

출처 및 근거

ORD 기록
ord-94cc5e6a289f47d2b4a6e9a041479a95
출처 데이터셋
uspto-grants-1976_06
특허 번호
US03966966

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