Carbon Dioxide → p-(2-Chlorophenyl)cinnamic acid

HRID 1659064Notes

Reaction equation

HRID 1659064 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:15]=[CH:14][C:11]([CH:12]=O)=[CH:10][CH:9]=1.C(O)(=O)[CH2:17][C:18]([OH:20])=[O:19].N1CCCCC1.C(=O)=O.Cl>N1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[CH:17][C:18]([OH:20])=[O:19])=[CH:10][CH:9]=1

Participants

7

Reactant 5

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 8082PiperidineHCID 13944002'-Chloro[1,1'-biphenyl]-4-carbaldehyde

Product 1

HCID 54534814p-(2-Chlorophenyl)cinnamic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineCatalyst

Procedure

A mixture of 21.6 g. (0.1 mole) of 4-(2'-chlorophenyl)benzaldehyde is heated on a steam bath with 13.2 g. of malonic acid and 95 ml. of pyridine containing 5 drops of piperidine. The mixture is heated for four hours until the liberation of carbon dioxide ceases. The cooled mixture is poured into a mixture of 110 ml. concentrated hydrochloric acid and 500 ml. of ice water. The solid which separates is filtered, washed and 15 ml. portions of cold water and then resuspended in 200 ml. of cold water, filtered, washed with cold water and dried at 40°C. The residue is then recrystallized from ethanol to obtain 4-(2'-chlorophenyl)cinnamic acid.

Workup

  1. additionA mixture of 21.6 g
  2. additionThe cooled mixture is poured into a mixture of 110 ml
  3. filtrationThe solid which separates is filtered
  4. washwashed
  5. filtrationof cold water, filtered
  6. washwashed with cold water
  7. customdried at 40°C
  8. customThe residue is then recrystallized from ethanol

Sources & evidence

ORD record
ord-892152934a76453b9e213d4fb110d525
Source dataset
uspto-grants-1976_06
Patent number
US03966801

Reaction notes

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