Benzyl Bromide → 4-(Benzyloxy)-2,6-dimethylbenzaldehyde

HRID 1013805Notes

Reaction equation

HRID 1013805 reaction equation
[CH3:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[C:6]([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+]>CN(C=O)C>[CH2:12]([O:10][C:8]1[CH:9]=[C:2]([CH3:1])[C:3]([CH:4]=[O:5])=[C:6]([CH3:11])[CH:7]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 5910722,6-Dimethyl-4-hydroxybenzaldehyde

Product 1

HCID 111608034-(Benzyloxy)-2,6-dimethylbenzaldehydeYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Treat a solution of 2,6-Dimethyl-4-hydroxybenzaldehyde (4.0 g, 27 mmol) and benzyl bromide (3.3 mL, 28 mmol) in DMF (50 mL) with Potassium carbonate (4.5 g, 32 mmol). Heat the reaction to 60° C. and stir for 1 hr. Cool the reaction and quench with 1N aqueous HCl. Extract the aqueous with Et2O. Wash the organic with brine, dry over MgSO4, and filter. Remove the solvent to afford 6.4 g (100%) of product. 1H NMR (d6-CDCl3) δ 10.46 (s, 1H), 7.31-7.43 (m, 5H), 6.65 (s, 2H), 5.08 (s, 2H), 2.58 (s, 6H).

Workup

  1. temperatureHeat
  2. customthe reaction to 60° C.
  3. temperatureCool
  4. customthe reaction
  5. customquench with 1N aqueous HCl
  6. extractionExtract the aqueous with Et2O
  7. washWash the organic with brine
  8. dry with materialdry over MgSO4
  9. filtrationfilter
  10. customRemove the solvent

Sources & evidence

ORD record
ord-900108a7406b4ba7b4a02113e1a7119f
Source dataset
uspto-grants-2011_07
Patent number
US07981918B2

Reaction notes

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