Piperonal → (e)-1-(3,4-Methylenedioxyphenyl)-3-(3,5-dimethoxyphenyl)prop-1-en-3-one

HRID 1817686Notes

Reaction equation

HRID 1817686 reaction equation
[CH:1]1[C:6]([CH:7]=O)=[CH:5][C:4]2[O:9][CH2:10][O:11][C:3]=2[CH:2]=1.[CH3:12][C:13]([C:15]1[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[C:17]([O:23][CH3:24])[CH:16]=1)=[O:14].[OH-].[Na+]>CO>[CH2:10]1[O:11][C:3]2[CH:2]=[CH:1][C:6](/[CH:7]=[CH:12]/[C:13]([C:15]3[CH:16]=[C:17]([O:23][CH3:24])[CH:18]=[C:19]([O:21][CH3:22])[CH:20]=3)=[O:14])=[CH:5][C:4]=2[O:9]1

Participants

5

Reactant 3

HCID 8438PiperonalHCID 14798Sodium Hydroxide3×HCID 959971-(3,5-Dimethoxyphenyl)ethan-1-one

Product 1

HCID 9944582(e)-1-(3,4-Methylenedioxyphenyl)-3-(3,5-dimethoxyphenyl)prop-1-en-3-oneYield 25.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of Piperonal (1.00 g, 6.67 mmol) and 3,5-dimethoxyacetophenone (1.20 g, 6.67 mmol) in methanol (30 ml) was added a 50% w/v solution of aqueous NaOH (8 ml, 15 eq). A colourless solution had formed initially following the dissolution of the two starting materials in the solvent, but upon addition of NaOH, the solution became a yellow, creamy suspension. A pale yellow precipitate was noticed approximately 2 or 3 mins after adding the aqueous NaOH. A further 3 ml (˜5 eq) of base was added, after 5 h, in order to drive the reaction to completion. The mixture was stirred for a total of 6 h at room temperature. The precipitate was collected via vacuum filtration and the filtrate discarded. The solid was purified by recrystallisation from hot methanol and hot filtration. The product was collected and allowed to be dried under vacuum to afford the title compound as a pale yellow solid (0.53 g, 25%). 1H-NMR (CDCl3) δ 7.25 (1H, d, CH(9)), 7.30(2H, d, CH(6&8)), 6.85 (1H, d, CH(3)), 6.65 (1H, t, CH(4)), 6.00 (2H, s, CH2(1)), 3.85 (6H, s, OCH3(5&7)); 13C-NMR (CDCl3) δ 189.958 (C═O), 160.870, 149.928, 148.401, 144.756, 140.403, 129.325, 125.221, 120.112, 108.650, 106.659, 106.253, 104.879, 101.621, 55.608 (OCH3); Infrared Spectrum Vmax (KBr)/cm−1 1668.3 (C═O); Mass Spectrum (FAB) m/e 313 (m+1); Elemental Analysis: Molecular Compound C18H16O5, calculated C=69.23, H=5.19 and found C=69.15, H=5.18.

Workup

  1. customA colourless solution had formed initially
  2. dissolutionthe dissolution of the two starting materials in the solvent
  3. custom2 or 3 mins
  4. customthe reaction to completion
  5. filtrationThe precipitate was collected via vacuum filtration
  6. filtrationThe solid was purified by recrystallisation from hot methanol and hot filtration
  7. customThe product was collected
  8. customto be dried under vacuum

Sources & evidence

ORD record
ord-789932bd0699427eb5307761d33614cd
Source dataset
uspto-grants-2009_10
Patent number
US07598294B2

Reaction notes

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