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

HRID 54972

반응식

HRID 54972 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0c4660183fbc41969b1652484277c365
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05624922

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