Benzyl Chloride → HCID 20282923, compound

HRID 463333Notes

Reaction equation

HRID 463333 reaction equation
O[C:2]1([OH:14])[C:9]([CH2:10][CH2:11][CH3:12])=[C:8]([OH:13])[CH:7]=[CH:6][CH:3]1[CH:4]=[O:5].[CH2:15](Cl)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.[I-].[K+]>[CH2:15]([O:13][C:8]1[C:9]([CH2:10][CH2:11][CH3:12])=[C:2]([OH:14])[C:3](=[CH:6][CH:7]=1)[CH:4]=[O:5])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 86739172HCID 86739172, compound

Product 1

HCID 20282923HCID 20282923, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 180AcetoneSolvent

Procedure

A mixture of 2,4-dihydroxy-3-propylsalicylaldehyde (15.5 g), benzyl chloride (12.0 g), potassium carbonate (13 g) and potassium iodide (0.5 g) in dry acetone (350 ml) was heated under reflux for 24 hours. The solid was removed by filtration and the solution evaporated to dryness. The oil obtained was distilled and the fraction bp0.5 mm 220-224° was collected to yield 15.0 g of 4-benzyloxy-3-propylsalicylaldehyde.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 24 hours
  3. customThe solid was removed by filtration
  4. customthe solution evaporated to dryness
  5. customThe oil obtained
  6. distillationwas distilled
  7. customthe fraction bp0.5 mm 220-224° was collected

Sources & evidence

ORD record
ord-3af35a978ce54543b5d28750abfc6e22
Source dataset
uspto-grants-1985_05
Patent number
US04518612

Reaction notes

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