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

HRID 1769117Notes

Reaction equation

HRID 1769117 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-eba79c607d4d46d8939b185d958588d9
Source dataset
uspto-grants-1995_01
Patent number
US05380721

Reaction notes

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