Benzaldehyde → 2-Propenoic acid, 3-phenyl-

HRID 1509366Notes

Reaction equation

HRID 1509366 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)[CH2:10][C:11]([OH:13])=[O:12].N1CCCCC1.N1C=CC=CC=1.Cl>>[C:11]([OH:13])(=[O:12])[CH:10]=[CH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 5

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 1049PyridineHCID 8082Piperidine

Product 1

HCID 87842-Propenoic acid, 3-phenyl-

Conditions

Temperature
80 °C

Procedure

Benzaldehyde (10 g, 94 mmol), malonic acid (2 eq.), and piperidine (0.1 eq.) were dissolved in pyridine (5 eq.) and stirred at 80° C. for 5 hours. After completion of the reaction, the reaction mixture was cooled down to the room temperature and neutralized with 3M HCl. The white solid thus obtained was filtered out and dried in a vacuum oven to yield cinnamic acid.

Workup

  1. customAfter completion of the reaction
  2. customThe white solid thus obtained
  3. filtrationwas filtered out
  4. customdried in a vacuum oven

Sources & evidence

ORD record
ord-9fa525317e2945e3ab8f466941e9d548
Source dataset
uspto-grants-2015_12
Patent number
US09223177B2

Reaction notes

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