Benzyl Bromide → 2-(Benzyloxy)-6-methoxybenzaldehyde

HRID 594365Notes

Reaction equation

HRID 594365 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH3:11])[C:3]=1[CH:4]=[O:5].[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH2:12]([O:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH3:11])[C:3]=1[CH:4]=[O:5])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 696926-Methoxysalicylaldehyde

Product 1

HCID 37354792-(Benzyloxy)-6-methoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of commercially available 2-hydroxy-6-methoxybenzaldehyde (1.000 g; 6.57 mmol), benzyl bromide (2.867 g; 16.43 mmol), and K2CO3 (2.960 g; 21.42 mmol) in anh. acetone (33 ml) was refluxed, under nitrogen, for 5.5 h. After cooling to rt, volatiles were removed under reduced pressure, and the residue was dissolved in water and AcOEt. The separated aq. layer was further extracted with AcOEt (2×), and the mixed organic layers were washed with brine, dried dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (heptane/AcOEt=8/2) afforded 2-(benzyloxy)-6-methoxybenzaldehyde. LC-MS (conditions E): tR=0.68 min.; [M+H]+: 243.27 g/mol.

Workup

  1. temperaturewas refluxed, under nitrogen, for 5.5 h
  2. customvolatiles were removed under reduced pressure
  3. dissolutionthe residue was dissolved in water
  4. extractionThe separated aq. layer was further extracted with AcOEt (2×)
  5. washthe mixed organic layers were washed with brine
  6. customdried
  7. dry with materialdried over anh. MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated to dryness under reduced pressure
  10. customPurification by FC (heptane/AcOEt=8/2)

Sources & evidence

ORD record
ord-69c8aa362c2d418e8b4ec400ce43e891
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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