Salicylaldehyde → HCID 10899688, compound

HRID 1249346Notes

Reaction equation

HRID 1249346 reaction equation
[CH:1](=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].C(=O)([O-])[O-].[K+].[K+].Br[CH:17]1[CH2:22][CH2:21][CH2:20][CH:19]=[CH:18]1>CC(C)=O>[CH:1]([C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[O:4][CH:22]1[CH2:21][CH2:20][CH2:19][CH:18]=[CH:17]1)=[O:9]

Participants

5

Reactant 3

HCID 6998SalicylaldehydeHCID 11430Potassium CarbonateHCID 1370573-Bromocyclohexene

Product 1

HCID 10899688HCID 10899688, compoundYield 92.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In a 10-liter reactor there were introduced 633.4 g (5.19 moles) of salicylaldehyde, 5 liters of acetone and 717.3 g of potassium carbonate, and the mixture was left with stirring at room temperature. After precipitation of the phenate, 836 g (5.19 moles) of 3-bromocyclohexene were rapidly added dropwise, and the mixture was brought to reflux for 21/2 hours. After removal of the inorganic salts by filtration, and evaporation of the solvent, the residue was taken up in ethyl ether, washed with 10% caustic soda and then water, and the ether phase was then dried over Na2SO4. After filtration and elimination of the ether, there were obtained 975 g of 3-(2-formylphenoxy)cyclohexene, which was used directly in the following stage.

Workup

  1. waitthe mixture was left
  2. additionwere rapidly added dropwise
  3. temperatureto reflux for 21/2 hours
  4. customAfter removal of the inorganic salts
  5. filtrationby filtration, and evaporation of the solvent
  6. washwashed with 10% caustic soda
  7. dry with materialwater, and the ether phase was then dried over Na2SO4
  8. filtrationAfter filtration and elimination of the ether

Sources & evidence

ORD record
ord-85daf6bea9884c8197cecc290f059289
Source dataset
uspto-grants-1986_12
Patent number
US04631277

Reaction notes

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