Benzaldehyde → (2-Methyl-1-naphthyl)(phenyl)methanol

HRID 54972

反応式

HRID 54972 の反応式
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH3:12].[Mg].[CH:14](=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1COCC1>[CH3:12][C:3]1[CH:4]=[CH:5][C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]=1[CH:14]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[OH:21]

参加物

5

反応物 3

HCID 240BenzaldehydeHCID 757541-Bromo-2-methylnaphthaleneHCID 5462224Magnesium

生成物 1

HCID 19957120(2-Methyl-1-naphthyl)(phenyl)methanol収率 78.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 10 g (45 mmol) of 1-bromo-2-methylnaphthalene in 75 mL of THF was refluxed with 1.2 g (50 mmol) of magnesium turnings for three hours. The reaction was cooled on ice and 4.8 mL (43 mmol) of benzaldehyde was added. The ice was removed, the reaction was stirred 45 minutes and quenched with 5 mL of 1N HCl followed by 50 mL of water. The reaction was extracted into ethyl acetate, dried over sodium sulfate and flash chromatographed through silica gel with 5-10% ethyl acetate in hexane to provide 8.4 g (75%) of 2-methyl-a-phenyl-1-naphthalenemethanol as a pale yellow gum.

後処理

  1. additionwas added
  2. customThe ice was removed
  3. customquenched with 5 mL of 1N HCl
  4. extractionThe reaction was extracted into ethyl acetate
  5. dry with materialdried over sodium sulfate and flash
  6. customchromatographed through silica gel with 5-10% ethyl acetate in hexane

出典と根拠

ORDレコード
ord-0c4660183fbc41969b1652484277c365
出典データセット
uspto-grants-1997_04
特許番号
US05624922

関連ノート

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