Potassium Carbonate → 3,5-Dibenzyloxybenzaldehyde

HRID 2248848Notes

Reaction equation

HRID 2248848 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].[C:7](Br)([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:8]>CC(C)=O>[CH2:7]([O:8][C:11]1[CH:10]=[C:9]([CH:14]=[C:13]([O:4][CH2:1][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:12]=1)[CH:7]=[O:8])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 12056Benzoyl bromide

Product 1

HCID 5613513,5-DibenzyloxybenzaldehydeYield 34%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a mixture of DHBD (24.4 g, 177 mmol) and potassium carbonate (12.2 g, 88.5 mmol) heated at reflux under argon in dry acetone (200 ml) was added dropwise over 12 hours a solution of BzBr (43.4 g, 30.2 ml, 248 mmol) in dry acetone (30 ml). Thin layer chromatography showed very little DHBD after the addition was complete. The reaction mixture was evaporated to dryness and the residue partitioned between dichloromethane/water. The aqueous layer was further extracted with dichloromethane (3×100 ml) and the combined dichloromethane layers extracted with aqueous sodium hydroxide (1N, 3×100 ml). Evaporation of the dichloromethane layers gave 18.1 g of essentially pure 3,5-dibenzyloxybenzaldehyde (34.0% based on DHBD). The sodium hydroxide extracts were acidified with glacial acetic acid, extracted with chloroform (3×100 ml), and the combined chloroform extracts dried and evaporated to dryness. The residue was recrystallized from methanol/water to give 14.5 g of compound XVI (36.0% based on DHBD).

Workup

  1. temperatureheated
  2. additionafter the addition
  3. customThe reaction mixture was evaporated to dryness
  4. customthe residue partitioned between dichloromethane/water
  5. extractionThe aqueous layer was further extracted with dichloromethane (3×100 ml)
  6. extractionthe combined dichloromethane layers extracted with aqueous sodium hydroxide (1N, 3×100 ml)
  7. customEvaporation of the dichloromethane layers

Sources & evidence

ORD record
ord-74a4fad2298249a18987857598505bf8
Source dataset
uspto-grants-1991_08
Patent number
US05041516

Reaction notes

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