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

HRID 54972

Reaction equation

HRID 54972 reaction equation
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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-0c4660183fbc41969b1652484277c365
Source dataset
uspto-grants-1997_04
Patent number
US05624922

Linked notes

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