Hydrochloric Acid → (5-Benzyloxy-2-bromo-4-methoxyphenyl)p-tolylmethanol

HRID 2381237Notes

Reaction equation

HRID 2381237 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([O:18][CH3:19])=[CH:11][C:12]([Br:17])=[C:13]([CH:16]=1)[CH:14]=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20]1([CH3:28])[CH:25]=[CH:24][C:23]([Mg]Br)=[CH:22][CH:21]=1.[Cl-].[NH4+].Cl>C(OCC)(=O)C.O1CCCC1>[CH2:1]([O:8][C:9]1[C:10]([O:18][CH3:19])=[CH:11][C:12]([Br:17])=[C:13]([CH:14]([C:23]2[CH:24]=[CH:25][C:20]([CH3:28])=[CH:21][CH:22]=2)[OH:15])[CH:16]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 109033195-(Benzyloxy)-2-bromo-4-methoxybenzaldehydeHCID 178418370HCID 178418370, compound

Product 1

HCID 67110063(5-Benzyloxy-2-bromo-4-methoxyphenyl)p-tolylmethanol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 5-benzyloxy-2-bromo-4-methoxy-benzaldehyde (1 g) and tetrahydrofuran (10 mL) was added p-tolylmagnesium bromide (1 mol/L tetrahydrofuran solution, 3.7 mL) under ice-salt bath cooling. After stirring at same temperature for 10 minutes, to the mixture were added an aqueous solution of ammonium chloride, ethyl acetate and 2 mol/L hydrochloric acid. The separated organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: 0%-50% ethyl acetate/hexane, gradient elution) to give the title compound (1.27 g).

Workup

  1. temperaturecooling
  2. dry with materialThe separated organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (eluent: 0%-50% ethyl acetate/hexane, gradient elution)

Sources & evidence

ORD record
ord-d14f0790052043b0990bc9b8ca0655a6
Source dataset
uspto-grants-2012_09
Patent number
US08258162B2

Reaction notes

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