Hydrochloric Acid → 3-Trifluoromethylcinnamic acid

HRID 1722229Notes

Reaction equation

HRID 1722229 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=O.C(O)(=O)[CH2:14][C:15]([OH:17])=[O:16].N1CCCCC1.Cl>N1C=CC=CC=1>[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=[CH:14][C:15]([OH:17])=[O:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 8082PiperidineHCID 679903-(Trifluoromethyl)benzaldehyde

Product 1

HCID 855273-Trifluoromethylcinnamic acidYield 96.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 3-(trifluoromethyl)benzaldehyde (25 g, 144 mmol), malonic acid (28.8 g, 277 mmol), anhydrous pyridine (100 ml) and piperidine (2 ml) was heated under reflux for 4 hours. The mixture was poured onto fresh ice (300 g) and concentrated hydrochloric acid (78 ml). The solid product was collected, dried and recrystallised (1:1 IMS/water) to give 30 g (96% of theory) of 3-(trifluoromethyl) cinnamic acid as off-white needles.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 hours
  3. customThe solid product was collected
  4. customdried
  5. customrecrystallised (1:1 IMS/water)

Sources & evidence

ORD record
ord-590694d638e347fead02d00815a6f477
Source dataset
uspto-grants-1989_08
Patent number
US04855086

Reaction notes

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