Hydrochloric Acid → 4,4-Diphenyl-3-butenoic acid

HRID 1651214Notes

Reaction equation

HRID 1651214 reaction equation
[C:1]1([CH:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:8]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(=O)[CH2:17][C:18]([OH:20])=[O:19].N1CCCCC1.Cl>N1C=CC=CC=1>[C:1]1([C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:8][CH2:17][C:18]([OH:20])=[O:19])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 8082PiperidineHCID 13696Diphenylacetaldehyde

Product 1

HCID 3483294,4-Diphenyl-3-butenoic acidYield 97.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of diphenylacetaldehyde (19.6 g), malonic acid (10.9 g) and piperidine (0.4 mL) in pyridine (20 mL) was heated at reflux until the evolution of gas had subsided (1.25 h). The solution was cooled and poured into a stirred mixture of ice (100 g) and 2N hydrochloric acid (150 mL). The resulting solid was recovered by filtration, washed with water and dried to provide 23.1 g of 4,4-diphenyl-3-butenoic acid, mp 109°-111° C. A portion was crystallized from ethyl acetate-hexane to give the pure acid of 4,4-diphenyl-3-butenoic acid, mp 112.5°-114° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux until the evolution of gas
  3. custom(1.25 h)
  4. temperatureThe solution was cooled
  5. filtrationThe resulting solid was recovered by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-d441bfeb7de343d88d68300089179ec6
Source dataset
uspto-grants-1990_05
Patent number
US04927838

Reaction notes

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