Hydrochloric Acid → Cinnamic Acid

HRID 1707408Notes

Reaction equation

HRID 1707408 reaction equation
[C:1]([OH:7])(=[O:6])[CH2:2][C:3](O)=O.N1CCCCC1.CS([C:18]1[CH:25]=[CH:24][C:21](C=O)=[CH:20][CH:19]=1)(=O)=O.Cl>O.N1C=CC=CC=1>[C:1]([OH:7])(=[O:6])/[CH:2]=[CH:3]/[C:18]1[CH:25]=[CH:24][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 8082PiperidineHCID 2203764-(Methylsulfonyl)benzaldehyde

Product 1

HCID 444539Cinnamic AcidYield 154%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

Combine 312 g (2.99 mole) of malonic acid, 506 mL of pyridine, 30 mL of piperidine and 300 g (1.49 mole) of p-methylsulfonyl-benzaldehyde and heat the mixture to 95°-100° C. for 4 h. Cool the mixture to room temperature and slowly pour into 3 L of a mixture of HCl, water and ice. Collect the resulting precipitate by filtration and dry the solid to give 340 g (83% yield) of the E-cinnamic acid derivative, m.p.=294°-296° C. 1H NMR (DMSO-d6, ppm): 7.96 (s, 4H); 7.78 (d, J=16 Hz, 1H); 6.71 (d, J=16 Hz, 1H); 3.5 (hr. s, 1H); 3.25 (s, 3H). ##STR15##

Workup

  1. customCollect the resulting precipitate
  2. filtrationby filtration
  3. customdry the solid

Sources & evidence

ORD record
ord-396d490dd52e435caa6ff92c703710db
Source dataset
uspto-grants-1994_10
Patent number
US05352832

Reaction notes

Loading…