Hydrochloric Acid → HCID 9884452, compound

HRID 1839534Notes

Reaction equation

HRID 1839534 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6](C=O)=[CH:5][CH:4]=1.[CH3:11][O:12][C:13]1[CH:14]=[C:15]([C:23](=[O:26])[CH2:24][CH3:25])[CH:16]=[C:17]([O:21][CH3:22])[C:18]=1[O:19][CH3:20].[OH-].[Na+].Cl.[CH3:30]O>>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6](/[CH:25]=[C:24](\[CH3:30])/[C:23]([C:15]2[CH:16]=[C:17]([O:21][CH3:22])[C:18]([O:19][CH3:20])=[C:13]([O:12][CH3:11])[CH:14]=2)=[O:26])=[CH:5][CH:4]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 312444-MethoxybenzaldehydeHCID 200101Propiophenone, 3',4',5'-trimethoxy-

Product 1

HCID 9884452HCID 9884452, compound

Procedure

To a stirred solution of 4-methoxybenzaldehyde (1.0 g, 7.3 mmol) and 1-(3,4,5-trimethoxyphenyl)propan-1-one (1.64 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 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 concentrated in vacuo. The product was purified by column chromatography using hexane/ethylacetate (4:1) as eluant, followed by recrystallisation from ethanol to afford the title compound as a pale yellow solid, 0.36 g (14%). 1H-NMR (CDCl3) δ 7.8 (1H, s), 7.6 (2H, m), 7.3 (2H, d), 7.0 (2H, d), 3.9 (9H, s), 3.8 (3H, s), 2.3 (3H, s). Mass Spectrum (FAB) m/e 343 (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. concentrationconcentrated in vacuo
  5. customThe product was purified by column chromatography
  6. customfollowed by recrystallisation from ethanol

Sources & evidence

ORD record
ord-8db180f256c44050a896384e3505ca42
Source dataset
uspto-grants-2004_01
Patent number
US06677383B1

Reaction notes

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