Potassium Carbonate → HCID 13343708, compound

HRID 1263287Notes

Reaction equation

HRID 1263287 reaction equation
[Cl:1][C:2]1[C:3]([OH:12])=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=[O:6].Br[CH:14]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC.C(Cl)(Cl)(Cl)Cl>[Cl:1][C:2]1[C:3]2[O:12][C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:5]([OH:6])[C:4]=2[CH:7]=[CH:8][C:9]=1[O:10][CH3:11]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 69637Diethyl bromomalonateHCID 133437063-Chloro-4-methoxysalicylaldehyde

Product 1

HCID 13343708HCID 13343708, compoundYield 79.6%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

To a solution of (14h) (69.91 g., 0.375 mol) and diethyl bromomalonate (79.9 ml., 0.468 mol) in 2-butanone (400 ml.) was added freshly powdered anhydrous potassium carbonate (51.78 g.). The suspension was stirred vigorously and heated at reflux for 4.5 hours, then filtered and evaporated to dryness. The oil obtained was redissolved in carbon tetrachloride and filtered, then evaporated and recrystallized from chloroform with hexane to yield 79.6% of (15h), m.p. 115.5°-117° C. Analysis (C15H17ClO7) C,H.

Workup

  1. temperatureheated
  2. temperatureat reflux for 4.5 hours
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe oil obtained
  6. filtrationfiltered
  7. customevaporated
  8. customrecrystallized from chloroform with hexane

Sources & evidence

ORD record
ord-227865f2b75f42aba53b75121c62af15
Source dataset
uspto-grants-1984_06
Patent number
US04456612

Reaction notes

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