Water → 2-(Benzyloxy)-5-iodobenzaldehyde

HRID 269593Notes

Reaction equation

HRID 269593 reaction equation
C(=O)([O-])[O-].[K+].[K+].[OH:7][C:8]1[CH:15]=[CH:14][C:13]([I:16])=[CH:12][C:9]=1[CH:10]=[O:11].[CH2:17](Cl)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O>CN(C)C=O>[CH2:17]([O:7][C:8]1[CH:15]=[CH:14][C:13]([I:16])=[CH:12][C:9]=1[CH:10]=[O:11])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 2526125-Iodosalicylaldehyde

Product 1

HCID 150434892-(Benzyloxy)-5-iodobenzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

67.2 g (0.48 mol) of potassium carbonate are added to a solution of 100 g (0.40 mol) of 2-hydroxy-5-iodobenzaldehyde (Example 1A) in 1.5 l of dimethylformamide and, after a few minutes, 51 ml (0.44 mol) of benzyl chloride are added. The reaction mixture is stirred under reflux at 120° C. for 24 h. After stirring at RT for a further 24 h and the addition of 1.5 l of water, a solid crystallizes out. The precipitate is collected by suction filtration, washed twice with water and dried in vacuo. The solid is recrystallized from 230 ml of ethanol. 122.9 g (90% of theory) of product are obtained.

Workup

  1. stirringAfter stirring at RT for a further 24 h
  2. customa solid crystallizes out
  3. filtrationThe precipitate is collected by suction filtration
  4. washwashed twice with water
  5. customdried in vacuo
  6. customThe solid is recrystallized from 230 ml of ethanol
  7. custom122.9 g (90% of theory) of product are obtained

Sources & evidence

ORD record
ord-9e94ef8973c342148286ee8d143e61ba
Source dataset
uspto-grants-2008_11
Patent number
US07446102B2

Reaction notes

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