Dimethylformamide → 2,5-Bis(benzyloxy)benzaldehyde

HRID 1171200Notes

Reaction equation

HRID 1171200 reaction equation
CN(C)[CH:3]=[O:4].[OH:6][C:7]1[CH:14]=[CH:13][C:12](O)=[CH:11][C:8]=1[CH:9]=[O:10].[H-].[Na+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>O>[CH2:18]([O:6][C:7]1[CH:14]=[CH:13][C:12]([O:4][CH2:3][C:7]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:8]=2)=[CH:11][C:8]=1[CH:9]=[O:10])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 709492,5-Dihydroxybenzaldehyde

Product 1

HCID 35303992,5-Bis(benzyloxy)benzaldehydeYield 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To an N,N-dimethylformamide (100 mL) solution of 2,5-dihydroxybenzaldehyde (10.0 g, 72.4 mmol) were added sodium hydride (5.79 g, 145 mmol) and benzyl bromide (18.9 mL, 159 mmol) at 0° C., which was stirred at room temperature for 24 hours. Water was added to the reaction solution at 0° C. followed by extraction with ethyl acetate. The organic layer was washed with water and sat. NaCl, followed by drying over anhydrous magnesium sulfate and filtering. The filtrate was concentrated under a reduced pressure and the residue was purified by silica gel column chromatography (heptane:ethyl acetate=4:1) to obtain the title compound (17.6 g, 76%) as a white solid.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with water and sat. NaCl
  3. dry with materialby drying over anhydrous magnesium sulfate
  4. filtrationfiltering
  5. concentrationThe filtrate was concentrated under a reduced pressure
  6. customthe residue was purified by silica gel column chromatography (heptane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-bfe41ff8def14a54ab1e22ddca4b87cc
Source dataset
uspto-grants-2010_11
Patent number
US07829585B2

Reaction notes

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