Carbon Dioxide → HCID 54063076, compound

HRID 1163994Notes

Reaction equation

HRID 1163994 reaction equation
[CH3:1][O:2][C:3]1[C:10]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:18])=[CH:9][CH:8]=[CH:7][C:4]=1[CH:5]=O.C(O)(=O)[CH2:20][C:21]([OH:23])=[O:22].N1CCCCC1.C(=O)=O.Cl>N1C=CC=CC=1.O>[CH3:1][O:2][C:3]1[C:10]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:18])=[CH:9][CH:8]=[CH:7][C:4]=1[CH:5]=[CH:20][C:21]([OH:23])=[O:22]

Participants

8

Reactant 5

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 8082PiperidineHCID 20513429HCID 20513429, compound

Product 1

HCID 54063076HCID 54063076, compoundYield 62.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

2-Methoxy-3-(2-chlorophenoxy)benzaldehyde (7.0 g) and malonic acid (5.60 g) were dissolved in pyridine (60 ml). To the solution was added piperidine (0.6 ml) and the mixture was heated gradually to 80° C., while carbon dioxide was produced. Thereafter, the mixture was refluxed under heating for 30 minutes. After cooling, the reaction mixture was poured into water (300 ml), acidified with conc. hydrochloric acid and extracted with diethyl ether. The extract was washed with water, dried over magnesium sulfate and then evaporated. The crystalline residue (7.10 g) was recrystallized from diisopropyl ether to give 3-[2-methoxy-3-(2-chlorophenoxy)phenyl]acrylic acid (5.1 g). mp 145°-147° C.

Workup

  1. customwas produced
  2. temperatureThereafter, the mixture was refluxed
  3. temperatureunder heating for 30 minutes
  4. temperatureAfter cooling
  5. extractionextracted with diethyl ether
  6. washThe extract was washed with water
  7. dry with materialdried over magnesium sulfate
  8. customevaporated
  9. customThe crystalline residue (7.10 g) was recrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-c4dcebebe6364bd487593c09495929b2
Source dataset
uspto-grants-1983_01
Patent number
US04367238

Reaction notes

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