Piperonal → HCID 9944581, compound

HRID 1817688Notes

Reaction equation

HRID 1817688 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]=[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]=[C:19]([O:21][CH3:22])[CH:18]=[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 709912',5'-Dimethoxyacetophenone

Product 1

HCID 9944581HCID 9944581, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of piperonal (1 g, 6.7 mmol) and 2,5-dimethoxyacetophenone (1.21 g, 6.7 mmol) in methanol (30 ml) was added 15 equivalents of aqueous sodium hydroxide (˜8 ml, 50% w/v) and the mixture stirred for 2 h. The resultant solid was collected by filtration and then recrystallised from methanol as fine, needle-like pale yellow crystals (1.70 g, 81%): mp 101° C.; 1H NMR δ (CDCl3) 3.78 (3H, s, OCH3), 3.85 (3H, s, OCH3), 6.00 (2H, s, CH2O), 6.83 (1H, d, ArH), 6.90 (1H, d, ArH), 7.00 (3H, m, ArH), 7.15 (1H, d, ArH), 7.23 (1H, d, J=15.7 Hz, ArH), 7.52 (1H, d, J=15.8 Hz, ArH); Infra red νmax (KBr)/cm−1 1652.9 (C═O); MS (rel intensity) m/z 313 ([M+H]+, 100%); Anal.

Workup

  1. filtrationThe resultant solid was collected by filtration
  2. customrecrystallised from methanol as fine, needle-like pale yellow crystals (1.70 g, 81%)

Sources & evidence

ORD record
ord-d527ed7e86944ad1ace5e37d88d0d36e
Source dataset
uspto-grants-2009_10
Patent number
US07598294B2

Reaction notes

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