Salicylaldehyde → HCID 21529337, compound

HRID 1658386Notes

Reaction equation

HRID 1658386 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:6]=[C:7]([CH:11]([CH3:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:8]=[CH:9][CH:10]=1)=[O:4].C(=O)([O-])[O-].[K+].[K+].[CH:24]1[CH:29]=[C:28]([CH:30]=O)[C:27]([OH:32])=[CH:26][CH:25]=1>C(O)C>[O:32]1[C:27]2[CH:26]=[CH:25][CH:24]=[CH:29][C:28]=2[CH:30]=[C:2]1[C:3]([C:5]1[CH:6]=[C:7]([CH:11]([CH3:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:8]=[CH:9][CH:10]=1)=[O:4]

Participants

5

Reactant 3

HCID 6998SalicylaldehydeHCID 11430Potassium CarbonateHCID 21529338HCID 21529338, compound

Product 1

HCID 21529337HCID 21529337, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 2-[meta-(α-bromo-acetyl)-phenyl]propionate (0.1 mole) is mixed with dry potassium carbonate (0.2 mole), salicylic aldehyde (0.1 mole) and ethanol (200 cc). The mixture is refluxed for 5 hours, with vigorous stirring. The initially yellow reaction medium turns brown during the heating step. The reaction mixture is then allowed to cool and the resulting precipitate is suction filtered. The alcohol is removed in vacuo. The resulting material is taken up into ethyl acetate, after which it is washed to neutral pH, dried and evaporated. The distilled residue gives a thick oil, b.p.0.05 = 210°-220°C. A second distillation gives the pure product (Yield: 25%).

Workup

  1. temperatureThe mixture is refluxed for 5 hours, with vigorous stirring
  2. temperatureto cool
  3. filtrationfiltered
  4. customThe alcohol is removed in vacuo
  5. washafter which it is washed to neutral pH
  6. customdried
  7. customevaporated
  8. customThe distilled residue gives a thick oil, b.p.0.05 = 210°-220°C
  9. distillationA second distillation

Sources & evidence

ORD record
ord-bcf48d2e70ce4a20b1933bb4d29115d1
Source dataset
uspto-grants-1976_06
Patent number
US03963758

Reaction notes

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