Benzaldehyde → 2-Propenoic acid, 3-phenyl-

HRID 38153Notes

Reaction equation

HRID 38153 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-bf1c9638c40543cd96f2a7e64ce8d0c8
Source dataset
uspto-grants-2013_09
Patent number
US08524721B2

Reaction notes

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