4-Hydroxybenzaldehyde → HCID 9883318, compound

HRID 1839532Notes

Reaction equation

HRID 1839532 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[CH3:10][C:11]([C:13]1[CH:18]=[C:17]([O:19][CH3:20])[C:16]([O:21][CH3:22])=[C:15]([O:23][CH3:24])[CH:14]=1)=[O:12].[OH-].[Na+].Cl>CO>[OH:1][C:2]1[CH:9]=[CH:8][C:5](/[CH:6]=[CH:10]/[C:11]([C:13]2[CH:14]=[C:15]([O:23][CH3:24])[C:16]([O:21][CH3:22])=[C:17]([O:19][CH3:20])[CH:18]=2)=[O:12])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 313Hydrochloric AcidHCID 143453',4',5'-TrimethoxyacetophenoneHCID 14798Sodium Hydroxide

Product 1

HCID 9883318HCID 9883318, compoundYield 5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 4-hydroxybenzaldehyde (1.0 g, 8.19 mmol) and 3,4,5-trimethoxyacetophenone (1.72 g, 8.19 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 column chromatography using hexane/ethyl acetate (7:3) as eluent to afford the title compound as a pale yellow solid (0.125 g, 5%). 1H-NMR (CDCl3) δ 7.8 (1H, d), 7.6 (2H, m), 7.4 (1H, s), 7.25 (2H, m), 6.9 (2H, d), 5.6 (1H, bs) 3.95 (9H, s). Mass Spectrum (FAB) m/e 315 (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

Sources & evidence

ORD record
ord-c5adb11e51324fa5b84ea416c65cd853
Source dataset
uspto-grants-2004_01
Patent number
US06677383B1

Reaction notes

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