Benzyl Bromide → Dibenzyloxybenzaldehyde

HRID 253448Notes

Reaction equation

HRID 253448 reaction equation
[OH:1][C:2]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[H-].[Na+].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C)C=O>[CH2:13]([O:1][C:2]1[C:9]([O:10][CH2:4][C:3]2[CH:6]=[CH:7][CH:8]=[CH:9][CH:2]=2)=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydride2×HCID 905792,3-Dihydroxybenzaldehyde

Product 1

HCID 10870855DibenzyloxybenzaldehydeYield 161.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,3-dihydroxybenzaldehyde (61, 25 g, 0.18 mol) in N,N-dimethylformamide (150 mL) tetrahydrofuran (250 mL), sodium hydride (7.24 g, 0.18 mol) was added at 0° C. under an atmosphere of nitrogen. The reaction mixture was allowed to warm to room temperature and was stirred at room temperature for 10 minutes. To the reaction mixture was then added benzyl bromide (54 mL, 0.45 mol). The reaction mixture was stirred at room temperature under an atmosphere of nitrogen for 3 hours, then cooled down to 0° C. Sodium hydride (8 g, 0.2 mol) was added to the reaction mixture. The reaction mixture was allowed to warm to room temperature and was stirred at room temperature overnight. The reaction mixture was poured into ice water and extracted with ethyl acetate. The organic layer was collected, washed with brine, and dried over magnesium sulfate. After removal of solvent, the residue was purified by silica gel column chromatography eluting with ethyl acetate in hexane to provide the compound as an off-white solid (128, 46.2 gm, 80%).

Workup

  1. stirringThe reaction mixture was stirred at room temperature under an atmosphere of nitrogen for 3 hours
  2. temperaturecooled down to 0° C
  3. temperatureto warm to room temperature
  4. stirringwas stirred at room temperature overnight
  5. extractionextracted with ethyl acetate
  6. customThe organic layer was collected
  7. washwashed with brine
  8. dry with materialdried over magnesium sulfate
  9. customAfter removal of solvent
  10. customthe residue was purified by silica gel column chromatography
  11. washeluting with ethyl acetate in hexane

Sources & evidence

ORD record
ord-19ab6a4f5efd4bfea792a73684a2b02d
Source dataset
uspto-grants-2011_01
Patent number
US07872018B2

Reaction notes

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