Malonic Acid → 3-(4-Phenylphenyl)prop-2-enoic acid

HRID 974021

Reaction equation

HRID 974021 reaction equation
[C:1]1([C:7]2[CH:14]=[CH:13][C:10]([CH:11]=O)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(=O)[CH2:16][C:17]([OH:19])=[O:18].N1CCCCC1>N1C=CC=CC=1>[C:1]1([C:7]2[CH:14]=[CH:13][C:10]([CH:11]=[CH:16][C:17]([OH:19])=[O:18])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 8082PiperidineHCID 76689(1,1'-Biphenyl)-4-carboxaldehyde

Product 1

HCID 254923-(4-Phenylphenyl)prop-2-enoic acidYield 76.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 4-phenylbenzaldehyde (5.17 g, 28.4 mmol), malonic acid (4.0 g), pyridine (20 ml), and piperidine (0.5 ml) was heated until gas evolution began. Heating was continued until gas evolution ceased (about 30 minutes at 90°-100° C.). The mixture was cooled, and the solid product triturated with boiling methanol (150 ml) and enough concentrated HCl to make the mixture acidic. The mixture was cooled, and the product collected by filtration, washed with water and methanol, and dried in vacuo to provide 4-phenylcinnamic acid (4.85 g, 76% yield), mp 220°-225° C. This material was dissolved in ethanol (150 ml) containing concentrated sulfuric acid (0.5 ml) and triethyl orthoacetate (3.5 ml), and refluxed for 24 hours. Removal of the solvent and recrystallization of the residue from methanol-water provided the ethyl ester (5.0 g, 92% yield), mp 88°-89° C.

Workup

  1. temperaturewas heated until gas evolution
  2. temperatureHeating
  3. custom(about 30 minutes at 90°-100° C.)
  4. temperatureThe mixture was cooled
  5. customthe solid product triturated with boiling methanol (150 ml) and enough concentrated HCl
  6. temperatureThe mixture was cooled
  7. filtrationthe product collected by filtration
  8. washwashed with water and methanol
  9. customdried in vacuo

Sources & evidence

ORD record
ord-e3f377d3f72849ed9be058409a8f0fd8
Source dataset
uspto-grants-1991_11
Patent number
US05066658

Linked notes

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