Carbon Dioxide → HCID 21495665, compound

HRID 1579790Notes

Reaction equation

HRID 1579790 reaction equation
[CH3:1][O:2][C:3]1[C:16]([C:17](=[O:25])[C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[CH:15][CH:14]=[CH:13][C:4]=1[CH2:5][CH:6](C(O)=O)[C:7]([OH:9])=[O:8].C(=O)=O>CCOCC>[Cl:24][C:21]1[CH:22]=[CH:23][C:18]([C:17]([C:16]2[C:3]([O:2][CH3:1])=[C:4]([CH2:5][CH2:6][C:7]([OH:9])=[O:8])[CH:13]=[CH:14][CH:15]=2)=[O:25])=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 280Carbon DioxideHCID 54243608HCID 54243608, compound

Product 1

HCID 21495665HCID 21495665, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

96.2 g of 2-methoxy-3-(p-chlorobenzoyl)-benzylmalonic acid were heated at 170°-195°C under an argon atmosphere and after the evolution of carbon dioxide gas, the mixture was cooled and added to 1 liter of ether. The acid mixture was extracted several times with 600 ml of a solution of 10% potassium carbonate and 150 ml of water. The combined aqueous phases were acidified with concentrated hydrochloric acid and the acid precipitate formed was extracted with ether. The combined ether phases were washed with water, dried over magnesium sulfate and evaporated to dryness under reduced pressure. The residue was crystallized from cyclohexane to obtain 56.8 g of 3-(3'-p-chlorobenzoyl-2'-methoxy-phenyl)-propionic acid in the form of colorless crystals.

Workup

  1. extractionThe acid mixture was extracted several times with 600 ml of a solution of 10% potassium carbonate and 150 ml of water
  2. customthe acid precipitate formed
  3. extractionwas extracted with ether
  4. washThe combined ether phases were washed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated to dryness under reduced pressure
  7. customThe residue was crystallized from cyclohexane

Sources & evidence

ORD record
ord-9c7ae0f53cfd432ca024ee9095c1ec75
Source dataset
uspto-grants-1976_01
Patent number
US03931302

Reaction notes

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