Piperonal → methyl(Z)-3-(3,4-methylenedioxyphenyl)-2-[3-(prop-1-yloxy)benzoyl]propenoate

HRID 863139Notes

Reaction equation

HRID 863139 reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH2:4][C:5](=[O:16])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH2:13][CH2:14][CH3:15])[CH:7]=1.[CH2:18]1[O:28][C:27]2[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][C:20]=2[O:19]1>C1C=CC=CC=1.C(O)(=O)C.N1CCCCC1>[CH2:18]1[O:28][C:27]2[CH:26]=[CH:25][C:22](/[CH:23]=[C:4](/[C:5](=[O:16])[C:6]3[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH2:13][CH2:14][CH3:15])[CH:7]=3)\[C:3]([O:2][CH3:1])=[O:17])=[CH:21][C:20]=2[O:19]1

Participants

6

Reactant 2

HCID 8438PiperonalHCID 10014332HCID 10014332, compound

Product 1

HCID 10090418methyl(Z)-3-(3,4-methylenedioxyphenyl)-2-[3-(prop-1-yloxy)benzoyl]propenoateYield 478.3%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 8082PiperidineCatalystHCID 241BenzeneSolvent

Procedure

To a solution of methyl-3-(Prop-1-yloxy)benzoylacetate (10 g, 4.2 mmol) in benzene (50 mL) was added 3,4-methylenedioxybenzaldehyde (6.36 g, 4.2 mmol) followed by piperidine (0.42 mL, 0.42 mmol) and glacial acetic acid (8 drops approx.). The mixture was refluxed for 2 h. and the volatiles removed in vacuo to give methyl (Z)-3-(3,4-methylenedioxyphenyl)-2-[3-(prop-1-yloxy)-benzoyl]propenoate (7.4 g, 48%) as an off white solid after titration with methanol (m.p. 122°-123° C.). Anal. Calc. for C21H20O6 : C, 68.47; H, 5.47. Found: C, 68.81; H, 5.49.

Workup

  1. temperatureThe mixture was refluxed for 2 h.
  2. customthe volatiles removed in vacuo

Sources & evidence

ORD record
ord-d866496fcc9e40a4aa73c8b85f829d2f
Source dataset
uspto-grants-1998_02
Patent number
US05719183

Reaction notes

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