Dimethylformamide → 2,3-Bis-(4-chloro-benzyloxy)-benzaldehyde

HRID 253401Notes

Reaction equation

HRID 253401 reaction equation
[OH:1][C:2]1[C:9](O)=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[H-].[Na+].[Cl:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Br)=[CH:16][CH:15]=1.CN(C)[CH:24]=[O:25]>O1CCCC1>[Cl:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18][O:1][C:2]2[C:9]([O:25][CH2:24][C:17]3[CH:20]=[CH:21][C:14]([Cl:13])=[CH:15][CH:16]=3)=[CH:8][CH:7]=[CH:6][C:3]=2[CH:4]=[O:5])=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 905792,3-Dihydroxybenzaldehyde

Product 1

HCID 580873042,3-Bis-(4-chloro-benzyloxy)-benzaldehydeYield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,3-dihydroxybenzaldehyde (61, 2.0 g, 14.5 mmol) in tetrahydrofuran (100 mL) was added sodium hydride (0.52 g, 13.0 mmol) at 0° C. under an atmosphere of nitrogen. The reaction mixture was allowed to warn to room temperature and was stirred at room temperature for 30 minutes. To the reaction mixture was then added 4-chlorobenzyl bromide (22, 2.7 g, 13.0 mmol). The reaction mixture was stirred at room temperature under an atmosphere of nitrogen overnight. N,N-dimethylformamide (50 mL) was added into the reaction mixture and it was stirred at room temperature for 24 hours. 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 (62, 2.3 gm, 46%).

Workup

  1. customto warn to room temperature
  2. stirringThe reaction mixture was stirred at room temperature under an atmosphere of nitrogen overnight
  3. stirringwas stirred at room temperature for 24 hours
  4. extractionextracted with ethyl acetate
  5. customThe organic layer was collected
  6. washwashed with brine
  7. dry with materialdried over magnesium sulfate
  8. customAfter removal of solvent
  9. customthe residue was purified by silica gel column chromatography
  10. washeluting with ethyl acetate in hexane

Sources & evidence

ORD record
ord-52a8627d0fb846d587bf8c5e0e8ffa38
Source dataset
uspto-grants-2011_01
Patent number
US07872018B2

Reaction notes

Loading…