Salicylaldehyde → o-(Allyloxy)benzaldehyde

HRID 1957465Notes

Reaction equation

HRID 1957465 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH:7](=[O:15])[C:8]1[C:9](=[CH:11][CH:12]=[CH:13][CH:14]=1)[OH:10].[CH2:16](Br)[CH:17]=[CH2:18]>>[CH2:18]([O:10][C:9]1[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=1[CH:7]=[O:15])[CH:17]=[CH2:16]

Participants

4

Reactant 3

HCID 6998SalicylaldehydeHCID 7841Allyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 101335o-(Allyloxy)benzaldehydeYield 91.1%

Procedure

Potassium carbonate (24.0 g, 173.9 mmol), was added to an ethanolic solution containing salicylaldehyde (19.0 g, 155.7 mmol), and allyl bromide (22.0 g, 181.8 mmol). The resulting suspension was heated to reflux overnight. The precipitated inorganic salt was filtered off. The filtrate was evaporated under reduced pressure to give the desired product, 2-allyloxy-benzaldehyde 23.0 g, yield 91%).

Workup

  1. temperatureThe resulting suspension was heated
  2. temperatureto reflux overnight
  3. filtrationThe precipitated inorganic salt was filtered off
  4. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-c4388b03854443c2ba57e77d5a14c477
Source dataset
uspto-grants-1998_07
Patent number
US05786123

Reaction notes

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