3',4',5'-Trimethoxyacetophenone → HCID 10155311, compound

HRID 2217070Notes

Reaction equation

HRID 2217070 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[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+]>CO.C(OCC)(=O)C>[OH:1][C:2]1[CH:3]=[C:4](/[CH:5]=[CH:13]/[C:14]([C:16]2[CH:17]=[C:18]([O:26][CH3:27])[C:19]([O:24][CH3:25])=[C:20]([O:22][CH3:23])[CH:21]=2)=[O:15])[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12]

Participants

6

Reactant 3

HCID 143453',4',5'-TrimethoxyacetophenoneHCID 14798Sodium HydroxideHCID 756794-Ethoxy-3-hydroxybenzaldehyde

Product 1

HCID 10155311HCID 10155311, compoundYield 16.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-hydroxy-4-ethoxybenzaldehyde (0.350 g, 2.5 mmol), 3,4,5-trimethoxyacetophenone (0.443 mg, 2.5 mmol) and 50% w/v of aqueous sodium hydroxide (3.37 ml, 0.042 mol) in methanol (5 ml) at room temperature for 18 h. An orange solid was isolated by filtration, dissolved in ethyl acetate which was subsequently dried over MgSO4 and reduced in vacuo. Purification by column chromatography (SiO2, petroleum:ether (40:60 v/v) with an increasing gradient of ethyl acetate) yielded 0.126 g (16.7%) of a yellow solid. 1H-NMR (CDCl3) δ 7.7 (d, 1H), 7.3 (m, 4H), 7.1 (dd, 1H), 6.9 (d, 1H), 5.75 (s, 1H), 4.2 (q, 2H), 3.95 (s×2, 9H), 1.5 (t, 3H). 13C-NMR (CDCl3) δ 190.0, 153.1, 150.0, 146.0, 133.7, 128.4. Mass Spectrum m/e (M+1) 359. Anal. Calcd. for C20H22O6: C, 67.03; H, 6.19. Found C, 66.74; H, 6.33.

Workup

  1. customAn orange solid was isolated by filtration
  2. dry with materialwas subsequently dried over MgSO4
  3. customPurification by column chromatography (SiO2, petroleum:ether (40:60 v/v) with an increasing gradient of ethyl acetate)

Sources & evidence

ORD record
ord-306f8a90f3014b369ba32b641616a18b
Source dataset
uspto-grants-2006_09
Patent number
US07112698B2

Reaction notes

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