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

HRID 650408Notes

Reaction equation

HRID 650408 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH:10]=[C:11]([C:16](=[O:27])[C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH2:24][CH2:25][CH3:26])[CH:18]=3)[C:12]([O:14][CH3:15])=[O:13])=[CH:4][C:3]=2[O:2]1.COC(=O)CC(=O)C1C=CC=C(OCCC)C=1.C1OC2C(=CC=C(C=2)C=O)O1>C1C=CC=CC=1.C(O)(=O)C.N1CCCCC1>[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5](/[CH:10]=[C:11](/[C:16](=[O:27])[C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH2:24][CH2:25][CH3:26])[CH:18]=3)\[C:12]([O:14][CH3:15])=[O:13])=[CH:4][C:3]=2[O:2]1

Participants

7

Reactant 3

HCID 8438PiperonalHCID 10014332HCID 10014332, compoundHCID 54237649HCID 54237649, compound

Product 1

HCID 10090418methyl(Z)-3-(3,4-methylenedioxyphenyl)-2-[3-(prop-1-yloxy)benzoyl]propenoateYield 48%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 8082PiperidineCatalystHCID 241BenzeneSolvent

Procedure

Methyl 3-(3,4 -methylenedioxyphenyl)-2-[3-(prop-1-yloxy)-benzoyl]propenoate. 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 trituration with methanol (m. p. 122-123° C.). Anal. Calc. for C21 H20O6: 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-ad81640110664e7e9808d32ca949bb03
Source dataset
uspto-grants-2001_08
Patent number
US06271399B1

Reaction notes

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