Benzaldehyde → 3-(3-Methoxypheny)-1-phenylpropanol

HRID 278161Notes

Reaction equation

HRID 278161 reaction equation
[CH:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:9][O:10][C:11]1[CH:12]=[C:13]([CH2:17][CH2:18][Mg]Br)[CH:14]=[CH:15][CH:16]=1.COC1C=C(CCBr)C=CC=1.[Mg]>C1COCC1>[CH3:9][O:10][C:11]1[CH:12]=[C:13]([CH2:17][CH2:18][CH:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[OH:8])[CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 1374501-Bromo-2-(3-methoxyphenyl)ethaneHCID 5462224MagnesiumHCID 178490129HCID 178490129, compound

Product 1

HCID 142247333-(3-Methoxypheny)-1-phenylpropanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of benzaldehyde (920 μl, 9 mmol) in dry THF (20 mL) was added slowly a solution of 2-(3-methoxyphenyl) ethylmagnesium bromide prepared from 2-(3-methoxyphenyl) ethyl bromide (2.1 g. 9.77 mmol) and magnesium (300 mg, 12 mmol). The mixture was stirred at room temperature for ½ hour then quenched with saturated NH4Cl. The mixture was then extracted into EtOAc, washed with H2O, dried (Na2SO4), filtered and concentrated in vacuo, then purified by silica gel chromatography (30% EtOAc/Hexane) to provide the desired product as a colorless viscous oil.

Workup

  1. customthen quenched with saturated NH4Cl
  2. extractionThe mixture was then extracted into EtOAc
  3. washwashed with H2O
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. custompurified by silica gel chromatography (30% EtOAc/Hexane)

Sources & evidence

ORD record
ord-3ee10c20dc3a44fabeb57aae702fd5f5
Source dataset
uspto-grants-2002_03
Patent number
US06358985B1

Reaction notes

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