Tetrahydrofuran → 2,6-Di-tert-butyl-4-[(2-methylcyclopenta-1,3-dien-1-yl)methyl]phenol

HRID 1980008노트

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HRID 1980008 반응식
[CH3:1][C:2]1[CH2:6][CH:5]=[CH:4][CH:3]=1.[C:7]([C:11]1[CH:16]=[C:15](N(C)C)[CH:14]=[C:13]([C:20]([CH3:23])([CH3:22])[CH3:21])[C:12]=1[OH:24])([CH3:10])([CH3:9])[CH3:8].O1CCC[CH2:26]1.[Na]>O>[CH3:1][C:2]1[CH:6]=[CH:5][CH2:4][C:3]=1[CH2:26][C:15]1[CH:16]=[C:11]([C:7]([CH3:10])([CH3:9])[CH3:8])[C:12]([OH:24])=[C:13]([C:20]([CH3:23])([CH3:22])[CH3:21])[CH:14]=1

참가 물질

6

반응물 4

HCID 8028TetrahydrofuranHCID 667751-Methyl-1,3-cyclopentadieneHCID 6193612,6-Di-t-butyl-4-dimethylaminophenol2회HCID 5360545Sodium

생성물 1

HCID 204379452,6-Di-tert-butyl-4-[(2-methylcyclopenta-1,3-dien-1-yl)methyl]phenol수율 90%

시약·촉매·용매 1

HCID 962Water용매

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온도
70 °C

실험 절차

To a stirred mixture of 40 g (0.5 m) methylcyclopentadiene, 39.5 g (0.15 m) 2,6-di-t-butyl-4-dimethylaminophenol and 100 ml of tetrahydrofuran was slowly added 6.0 g (0.26 m) of sodium. The temperature was raised to 70° C. and the mixture allowed to react for 20 hours. A gas chromatograph showed that all of the 2,6-di-t-butyl-4-dimethylaminophenol had reacted. The mixture was diluted with water, extracted with toluene and rotovaped to remove the toluene and leave 38 g of crude product. A 90% yield, 31.5 g, of pure product methyl-(3,5-di-tert-butyl-4-hydroxybenzyl)cyclopentadiene was obtained by distillation, b.p. 155° to 160° C. at 1.5 mm as a viscous yellow oil. After standing at room temperature for 2 weeks, the material was analyzed by mass spectral analysis and by gas chromatography. Both showed that the product and its dimer were present. The mass spectrum showed a 3 to 1 ratio of the monomer to dimer, m/e 298 and m/e 596, respectively. The gas chromatograph showed a sharp peak for the monomer followed by the broad peak due to the slow decomposition of the dimer.

후처리

  1. customto react for 20 hours
  2. customhad reacted
  3. extractionextracted with toluene
  4. customto remove the toluene
  5. customleave 38 g of crude product

출처 및 근거

ORD 기록
ord-8ced1c6af419476180317c692fb3b1f0
출처 데이터셋
uspto-grants-1984_11
특허 번호
US04484010

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