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

HRID 1065464Notes

Reaction equation

HRID 1065464 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[Cl:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH2:22]Cl>O.C(O)C>[Cl:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH2:22][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 12103m,alpha-Dichlorotoluene

Product 1

HCID 7354654-[(3-Chlorophenyl)methoxy]benzaldehyde

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

The starting material is prepared as follows: To the stirring mixture of 244 g of p-hydroxybenzaldehyde, 360 g of potassium carbonate, 32 g of potassium iodide, 1.2 lt of 95% aqueous ethanol and 160 ml of water is added slowly 367 g of m-chlorobenzyl chloride. The mixture is stirred at reflux for four hours, cooled to 80° and 2 lt of warm water are added while stirring. The mixture is cooled, the precipitate collected, washed with water and recrystallized from methanol, to afford the 4-(3-chlorobenzyloxy)-benzaldehyde melting at 51°-54°.

Workup

  1. customThe starting material is prepared
  2. temperatureat reflux for four hours
  3. temperaturecooled to 80°
  4. stirringwhile stirring
  5. temperatureThe mixture is cooled
  6. customthe precipitate collected
  7. washwashed with water
  8. customrecrystallized from methanol

Sources & evidence

ORD record
ord-7c76cb8eaf9242d0b57d336c93738823
Source dataset
uspto-grants-1982_05
Patent number
US04329367

Reaction notes

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