Malonic Acid → 3-Butenoic acid, 4-phenyl-, (3E)-

HRID 1506973Notes

Reaction equation

HRID 1506973 reaction equation
[C:1]1([CH2:7][CH:8]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(=O)[CH2:11][C:12]([OH:14])=[O:13].N1CCCCC1>N1C=CC=CC=1>[C:1]1(/[CH:7]=[CH:8]/[CH2:11][C:12]([OH:14])=[O:13])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 998PhenylacetaldehydeHCID 8082Piperidine

Product 1

HCID 53706253-Butenoic acid, 4-phenyl-, (3E)-Yield 66.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of 2-phenylacetaldehyde (5.0 g, 32.3 mmol) and malonic acid (4.0 g, 38.8 mmol) in pyridine (25.0 mL) was added a catalytic amount of piperidine (0.64 mL, 6.46 mmol) then heated to reflux. After 3 h, the resulting mixture was cooled to room temperature and concentrated under reduced pressure. The crude product was slowly added 2N HCl. The white precipitate was filtered off and dried under vacuum to produce the title compound (3.5 g, 55˜80%)

Workup

  1. temperaturethen heated to reflux
  2. concentrationconcentrated under reduced pressure
  3. filtrationThe white precipitate was filtered off
  4. customdried under vacuum

Sources & evidence

ORD record
ord-64823d04823941d18444dd0bac49495d
Source dataset
uspto-grants-2015_12
Patent number
US09221783B2

Reaction notes

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