Benzaldehyde → 2-Propenoic acid, 3-phenyl-

HRID 562682Notes

Reaction equation

HRID 562682 reaction equation
[C:1]([OH:7])(=[O:6])[CH2:2][C:3](O)=O.C(=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.N1CCCCC1.Cl>N1C=CC=CC=1.O>[C:1]([OH:7])(=[O:6])[CH:2]=[CH:3][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 8082Piperidine

Product 1

HCID 87842-Propenoic acid, 3-phenyl-

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of malonic acid (10.4 g, 0.1 mol) and the benzaldehyde (0.05 mol) in pyridine (20 mL) was added neat piperidine (0.75 mL, 7.6 mmol). The reaction mixture was stirred at 80° C. for 17 hr, chilled, then added to 200 mL cold water. This mixture was acidified with conc. HCl (25 mL) and the white precipitate collected by filtration, washed with 5×10 mL water, and dried to give pure cinnamic acid in typical yields of >95%.

Workup

  1. temperaturechilled
  2. filtrationthe white precipitate collected by filtration
  3. washwashed with 5×10 mL water
  4. customdried

Sources & evidence

ORD record
ord-44339a58a64b46829c8fdcbb24d5559b
Source dataset
uspto-grants-2011_11
Patent number
US08067428B2

Reaction notes

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