Potassium Carbonate → HCID 13343708, compound

HRID 1154590Notes

Reaction equation

HRID 1154590 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, compound

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 yeild 79.6% of (15h), m.p. 115°-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 to yeild 79.6% of (15h), m.p. 115°-117° C

Sources & evidence

ORD record
ord-107321f3f3d849f8a7bdc3daec2951c6
Source dataset
uspto-grants-1984_12
Patent number
US04490384

Reaction notes

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