Water → HCID 15458749, compound

HRID 1358540Notes

Reaction equation

HRID 1358540 reaction equation
[CH:1](=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[CH:10](=[O:18])[CH:11]=[CH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].C(=O)([O-])[O-].[K+].[K+].O>O1CCOCC1>[CH2:13]([CH:12]1[C:11]([CH:10]=[O:18])=[CH:1][C:2]2[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=2[O:4]1)[CH2:14][CH2:15][CH2:16][CH3:17]

Participants

6

Reactant 4

HCID 962WaterHCID 6998SalicylaldehydeHCID 11430Potassium CarbonateHCID 169002-Octenal

Product 1

HCID 15458749HCID 15458749, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 22.0 g (0.18 mol) of salicylaldehyde, 25.0 g (0.198 mol) of 2-octenal and 24.8 g (0.18 mol) of potassium carbonate in 200 ml of dioxane, maintained under an inert atmosphere, is heated at reflux for 2.5 h. The reaction mixture is subsequently brought to room temperature (20-25° C.) and then diluted by addition of 1.5 litres of water. The formation of an oil is observed, which oil is extracted with methylene chloride. The organic phase is dried over anhydrous sodium sulphate and then concentrated under reduced pressure. The title compound is thus obtained in a form of an orange oil, which oil is distilled under reduced pressure (B.p. (0.44 mm Hg): 132-140° C.). 20 g of the title product are obtained by distillation (48% yield).

Workup

  1. temperaturemaintained under an inert atmosphere
  2. temperatureis heated
  3. temperatureat reflux for 2.5 h
  4. customis subsequently brought to room temperature
  5. custom(20-25° C.)
  6. extractionwhich oil is extracted with methylene chloride
  7. dry with materialThe organic phase is dried over anhydrous sodium sulphate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-98a9fa77fd8d43a69c9de7f2d67fc31a
Source dataset
uspto-grants-2003_07
Patent number
US06596758B1

Reaction notes

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