Hydrochloric Acid → alpha-Methyl-4-nitrocinnamic acid

HRID 981891

Reaction equation

HRID 981891 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:12][CH:13](C(O)=O)[C:14]([OH:16])=[O:15].N1CCCCC1.Cl>N1C=CC=CC=1>[CH3:12][C:13](=[CH:8][C:7]1[CH:10]=[CH:11][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)[C:14]([OH:16])=[O:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 487Methylmalonic AcidHCID 5414-NitrobenzaldehydeHCID 8082Piperidine

Product 1

HCID 235115alpha-Methyl-4-nitrocinnamic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

630 ml of pyridine was added to 76 g of 4-nitrobenzaldehyde (m.p. 105°-106.5° C.), 118 g of methylmalonic acid (prepared by hydrolysis of diethyl methylmalonate) and 85 g of piperidine. The mixture was heated with stirring over a steam bath for 24 hours. After being allowed to cool, the reaction mixture was then added to a mixture of 1,250 ml of concentrated hydrochloric acid and 2.5 kg of ice. The resulting oil content was then extracted with diethyl ether. The oil content was further extracted with a 5% aqueous solution of sodium hydroxide. The aqueous solution was then slightly acidified. The resulting crystal composition was then filtered off and dried. (Yield: 86 g (83%))

Workup

  1. temperatureThe mixture was heated
  2. temperatureto cool
  3. extractionThe resulting oil content was then extracted with diethyl ether
  4. extractionThe oil content was further extracted with a 5% aqueous solution of sodium hydroxide
  5. filtrationThe resulting crystal composition was then filtered off
  6. customdried

Sources & evidence

ORD record
ord-15d003794798414d8244bb38881d6034
Source dataset
uspto-grants-1991_02
Patent number
US04994363

Linked notes

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