Malonic Acid → 3-[3-(Cyclopropyloxy)phenyl]-2-propenoic acid

HRID 1893629Notes

Reaction equation

HRID 1893629 reaction equation
[CH:1]1([O:4][C:5]2[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=2)[CH:8]=O)[CH2:3][CH2:2]1.C(O)(=O)[CH2:14][C:15]([OH:17])=[O:16].N1CCCCC1>N1C=CC=CC=1>[CH:1]1([O:4][C:5]2[CH:6]=[C:7]([CH:8]=[CH:14][C:15]([OH:17])=[O:16])[CH:10]=[CH:11][CH:12]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 8082PiperidineHCID 577854763-(Cyclopropyloxy)benzaldehyde

Product 1

HCID 686183603-[3-(Cyclopropyloxy)phenyl]-2-propenoic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-cyclopropoxybenzaldehyde (7.51 g, 46.3 mmol) was dissolved in pyridine (195 mL) then malonic acid (19.3 g, 185 mmol) and piperidine (6.86 mL, 69.5 mmol) were added. The reaction was stirred at reflux for 2 hr then concentrated. The residue was poured on to ice cold 6N HCl and decanted to collect the solution. The solution was diluted with DCM and extracted with DCM. The extract and the solid from the water layer were combined and basified with 2N NaOH. The basic solution was washed with DCM, acidified and filtered to give 3-(3-cyclopropoxy-phenyl)-acrylic acid as white solid: 1H NMR (CDCl3, 300 MHz) δ 7.77 (d, 1H), 7.36-7.09 (m, 4H), 6.44 (d, 1H), 3.77 (m, 1H), 0.81 (m, 4H).

Workup

  1. temperatureat reflux for 2 hr
  2. concentrationthen concentrated
  3. additionThe residue was poured on to ice cold 6N HCl
  4. customdecanted
  5. customto collect the solution
  6. additionThe solution was diluted with DCM
  7. extractionextracted with DCM
  8. extractionThe extract
  9. washThe basic solution was washed with DCM
  10. filtrationfiltered

Sources & evidence

ORD record
ord-466742b820ba4b9c82ca5890db07e25d
Source dataset
uspto-grants-2013_08
Patent number
US08513186B2

Reaction notes

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