Hydrochloric Acid → 4,6-Di-tert-butyl-5-hydroxybenzofuran

HRID 1900526노트

반응식

HRID 1900526 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:10][C:11]1[C:12]([C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:13][C:14]2[O:18][C:17](CCCCCCCC)=[CH:16][C:15]=2[C:27]=1[C:28]([CH3:31])([CH3:30])[CH3:29])(=O)C.O.Cl>O1CCCC1>[C:28]([C:27]1[C:15]2[CH:16]=[CH:17][O:18][C:14]=2[CH:13]=[C:12]([C:32]([CH3:35])([CH3:34])[CH3:33])[C:11]=1[OH:10])([CH3:31])([CH3:30])[CH3:29]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 184331765-Acetoxy-4,6-di-tert-butyl-2-octylbenzofuranHCID 21226445Aluminium lithium hydride

생성물 1

HCID 117707334,6-Di-tert-butyl-5-hydroxybenzofuran수율 132.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

Lithium aluminum hydride (0.26 g) was suspended in tetrahydrofuran (50 ml) under a nitrogen atmosphere and a solution of 5-acetoxy-4,6-di-tert-butyl-2-octylbenzofuran (2.7 g) in tetrahydrofuran (20 ml) was added to the suspension under cooling with ice. After heating under reflux for 3 h, the mixture was cooled to room temperature and water was added dropwise. After adding 10% aqueous HCl (50 ml), the mixture was subjected to extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated. The concentrate was purified by silica gel chromatography (10% ethyl acetate in n-hexane) to afford 4,6-di-tert-butyl-5-hydroxybenzofuran [2.2 g (yield, 92%)] as a colorless oil.

후처리

  1. temperatureunder cooling with ice
  2. temperatureAfter heating
  3. temperatureunder reflux for 3 h
  4. extractionthe mixture was subjected to extraction with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe concentrate was purified by silica gel chromatography (10% ethyl acetate in n-hexane)

출처 및 근거

ORD 기록
ord-0f2d93b2e1534167bb2d8d5d405e3898
출처 데이터셋
uspto-grants-1996_11
특허 번호
US05574178

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