Hydrochloric Acid → HCID 9905484, compound

HRID 1839530Notes

Reaction equation

HRID 1839530 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.[CH3:11][C:12]([C:14]1[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=1)=[O:13].[OH-].[Na+].Cl>CO>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6](/[CH:7]=[CH:11]/[C:12]([C:14]2[CH:15]=[C:16]([O:24][CH3:25])[C:17]([O:22][CH3:23])=[C:18]([O:20][CH3:21])[CH:19]=2)=[O:13])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 143453',4',5'-TrimethoxyacetophenoneHCID 14798Sodium HydroxideHCID 312444-Methoxybenzaldehyde

Product 1

HCID 9905484HCID 9905484, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 4-methoxybenzaldehyde (1.0 g, 7.3 mmol) and 3,4,5-trimethoxyacetophenone (1.54 g, 7.3 mmol) in methanol (30 ml) was added a 50% w/v solution of aqueous NaOH (1 ml). The mixture was stirred for 24 h 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 column chromatography followed by recrystallisation from methanol to afford the title compound as a pale yellow solid 1.22 g (51%). 1H NMR (CDCl3) δ 7.8 (1H, d), 7.6 (2H, m), 7.4 (1H, d), 7.3 (2H, d), 7.0 (2H, d), 3.9 (9H, s), 3.8 (3H s). Mass Spectrum (FAB) m/e 329 (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 column chromatography
  6. customfollowed by recrystallisation from methanol

Sources & evidence

ORD record
ord-e49bc33c4cac41ce98008432f5d8fe9c
Source dataset
uspto-grants-2004_01
Patent number
US06677383B1

Reaction notes

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