4-Hydroxybenzaldehyde → 4-[(3-Fluorophenyl)methoxy]benzaldehyde

HRID 658805Notes

Reaction equation

HRID 658805 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5]Cl.[OH:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=[O:16])=[CH:13][CH:12]=1.[OH-].[Na+]>C(O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][O:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=[O:16])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 99743-Fluorobenzyl chlorideHCID 14798Sodium Hydroxide

Product 1

HCID 8801194-[(3-Fluorophenyl)methoxy]benzaldehydeYield 101.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Accordingly, 3-fluorobenzyl chloride (14.5 g, 100 mmol) is added under stirring and under nitrogen atmosphere to a solution of 4-hydroxybenzaldehyde (12.2 g, 100 mmol) and of NaOH (4.0 g, 100 mmol) in ethanol (100 mL). The mixture is gradually heated in 25 minutes to reflux and stirred at reflux temperature for 6 hours and 20 minutes. The reaction mixture is filtrated and then concentrated at reduced pressure to obtain 4-(3-fluoro-benzyloxy)benzaldehyde (23.43 g) as a yellow solid residue. Dichloromethane (250 mL) is added to the residue, the insoluble is filtered and the resulting solution is concentrated under reduced pressure to provide 4-(3-fluorobenzyloxy)benzaldehyde as a yellow solid, in 80.4% yield.

Workup

  1. temperatureThe mixture is gradually heated in 25 minutes
  2. temperatureto reflux
  3. temperatureat reflux temperature for 6 hours
  4. custom20 minutes
  5. filtrationThe reaction mixture is filtrated
  6. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-3bc27e15950b4f57831619399a611f63
Source dataset
uspto-grants-2011_12
Patent number
US08076515B2

Reaction notes

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