Potassium Carbonate → HCID 14677663, compound

HRID 2073599Notes

Reaction equation

HRID 2073599 reaction equation
[Cl:1][C:2]1[C:9]([Cl:10])=[CH:8][CH:7]=[C:4]([CH:5]=O)[C:3]=1[OH:11].Cl[CH:13](C(OC)=O)[C:14]([O:16][CH3:17])=[O:15].C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[Cl:10][C:9]1[CH:8]=[CH:7][C:4]2[CH:5]=[C:13]([C:14]([O:16][CH3:17])=[O:15])[O:11][C:3]=2[C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 120070Dimethyl chloromalonateHCID 5283863,4-Dichloro-2-hydroxybenzaldehyde

Product 1

HCID 14677663HCID 14677663, compoundYield 75.5%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A suspension of 3,4-dichlorosalicylaldehyde (191 mg, 1.0 mmol), dimethyl chloromalonate (330 mg, 2.0 mmol), and powdery anhydrous potassium carbonate (414 mg, 3.0 mmol) in 4 ml of methyl ethyl ketone is refluxed under heating for 3 hours and evaporated under reduced pressure. The remaining residue is dissolved in ethyl acetate, washed with 10% hydrochloric acid, then water, dried over anhydrous sodium sulfate, and evaporated under reduced pressure to give a residue, which is chromatographed on a silca gel with methylene chloride as an eluent. The eluates are recrystallized from an ethyl acetate-diethyl ether solution to give 185 mg (Yield 75.2%) of methyl 6,7-dichloro-2-benzofurancarboxylate (D-1), m.p. 161.5°-162° C.

Workup

  1. temperatureis refluxed
  2. temperatureunder heating for 3 hours
  3. customevaporated under reduced pressure
  4. dissolutionThe remaining residue is dissolved in ethyl acetate
  5. washwashed with 10% hydrochloric acid
  6. dry with materialwater, dried over anhydrous sodium sulfate
  7. customevaporated under reduced pressure
  8. customto give a residue, which
  9. customis chromatographed on a silca gel with methylene chloride as an eluent
  10. customThe eluates are recrystallized from an ethyl acetate-diethyl ether solution

Sources & evidence

ORD record
ord-4c8941d6d4ef4c05a34be22ba79955e0
Source dataset
uspto-grants-1990_04
Patent number
US04918206

Reaction notes

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