Hydrochloric Acid → HCID 6214039, compound

HRID 1839533Notes

Reaction equation

HRID 1839533 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:4]=1[CH:5]=O.[CH3:13][C:14]([C:16]1[CH:21]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH3:25])=[C:18]([O:26][CH3:27])[CH:17]=1)=[O:15].[OH-].[Na+].Cl>CO>[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:4]=1/[CH:5]=[CH:13]/[C:14]([C:16]1[CH:17]=[C:18]([O:26][CH3:27])[C:19]([O:24][CH3:25])=[C:20]([O:22][CH3:23])[CH:21]=1)=[O:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 143453',4',5'-TrimethoxyacetophenoneHCID 14798Sodium HydroxideHCID 691752,4-Dimethoxybenzaldehyde

Product 1

HCID 6214039HCID 6214039, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 2,4-dimethoxybenzaldehyde (1 g, 6.00 mmol) and 3,4,5-trimethoxyacetophenone (1.27 g, 6.00 mmol) in methanol (30 ml) was added a 50% w/v solution of aqueous NaOH (1 ml). The mixture was stirred for 24 hours at room temperature, acidified with 2N HCl and extracted with ethyl acetate (3×30 ml). The combined organic phase was dried over anhydrous MgSO4, filtered, and the solvent evaporated in vacuo. The product was purified by recrystallisation from ethanol to afford the title compound as a pale yellow solid, 1.67 g (78%). 1H-NMR (CDCl3) δ 8.0 (1H, d), 7.5 (1H, d), 7.4 (1H, d), 7.2 (2H, s), 6.6 (1H, dd), 6.5 (1H, d), 3.9 (9H, d), 3.85 (3H, s), 3.83 (3H, s). Mass Spectrum (FAB) m/e 359 (M+1).

Workup

  1. extractionextracted with ethyl acetate (3×30 ml)
  2. dry with materialThe combined organic phase was dried over anhydrous MgSO4
  3. filtrationfiltered
  4. customthe solvent evaporated in vacuo
  5. customThe product was purified by recrystallisation from ethanol

Sources & evidence

ORD record
ord-fe6a7901d4bb494b8567e307440ad0af
Source dataset
uspto-grants-2004_01
Patent number
US06677383B1

Reaction notes

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