Piperonal → HCID 5319619, compound

HRID 1817687Notes

Reaction equation

HRID 1817687 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]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][C:16]=1[O:23][CH3:24])=[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:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][C:16]=3[O:23][CH3:24])=[O:14])=[CH:5][C:4]=2[O:9]1

Participants

5

Reactant 3

HCID 8438PiperonalHCID 14798Sodium HydroxideHCID 700161-(2,4-Dimethoxyphenyl)ethanone

Product 1

HCID 5319619HCID 5319619, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of piperonal (1 g, 6.7 mmol) and 2,4-dimethoxyacetophenone (1.21 g, 6.7 mmol) in methanol (30 ml) was added 20 equivalents of aqueous sodium hydroxide (˜11 ml, 50% w/v) and the mixture stirred for 2 h. The resultant solid was collected by filtration and then recrystallised from methanol as pale yellow crystals (0.86 g, 41%): mp 137° C.; 1H NMR δ (CDCl3) 3.9 (3H, s, OCH3), 3.92 (3H, s, OCH3), 6.01 (2H, s, CH2O), 6.50 (2H, dd, ArH), 6.80 (1H, d, ArH), 7.00 (2H, m, ArH), 7.25 (1H, d, J=15.7 Hz, ArH), 7.59 (1H, d, J=15.7 Hz, ArH), 7.70 (1H, d, ArH); 13C NMR δ 101.45, 122.35, 129.93, 148.23, 149.37, 160.29, 164.05, 190.34; Infra red νMAX (KBr)/cm−1 1659.6 (C═O); MS (rel intensity) m/z 313 ([M+H]+, 37%); Anal. Calcd (CO18H16O5): C, 69.23; H, 5.13. Found C, 68.97; H, 5.26.

Workup

  1. filtrationThe resultant solid was collected by filtration
  2. customrecrystallised from methanol as pale yellow crystals (0.86 g, 41%)

Sources & evidence

ORD record
ord-f47dfcd1af454317b564f007eb5e75c0
Source dataset
uspto-grants-2009_10
Patent number
US07598294B2

Reaction notes

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