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

HRID 1980008ノート

反応式

HRID 1980008 の反応式
[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

参加物

6

反応物 4

HCID 8028TetrahydrofuranHCID 667751-Methyl-1,3-cyclopentadieneHCID 6193612,6-Di-t-butyl-4-dimethylaminophenol2 回HCID 5360545Sodium

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
70 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8ced1c6af419476180317c692fb3b1f0
出典データセット
uspto-grants-1984_11
特許番号
US04484010

反応ノート

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