3',4',5'-Trimethoxyacetophenone → HCID 6212878, compound

HRID 2217067Notes

Reaction equation

HRID 2217067 reaction equation
[CH2:1]([O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1)[CH2:2][CH3:3].[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>[CH2:1]([O:4][C:5]1[CH:12]=[CH:11][C:8](/[CH:9]=[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:6]=1)[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 143453',4',5'-TrimethoxyacetophenoneHCID 14798Sodium HydroxideHCID 798124-Propoxybenzaldehyde

Product 1

HCID 6212878HCID 6212878, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 4-propoxybenzaldehyde (1.5 ml, 9.5 mmol) and 3,4,5-trimethoxyacetophenone (2.0 g, 9.5 mmol) in methanol (30 ml) was added 50% w/v of aqueous sodium hydroxide (7.6 ml, 0.095 mol). The reaction was stirred for 24 h at room temperature. A precipitate was isolated by filtration, washed with pet:ether and subsequently recrystallised from ethanol to give 0.9 g (27%) of a pale yellow powder. 1H-NMR (CDCl3) δ 7.8 (d, 1H), 7.6 (d, 2H), 7.3 (d, 1H), 7.2 (m, 1H), 6.8 (d, 2H), 3.95 (m, 2H), 3.9 (s×2, 9H), 1.8 (t, 2H), 1.0 (t, 3H).

Workup

  1. customA precipitate was isolated by filtration
  2. washwashed with pet
  3. customether and subsequently recrystallised from ethanol

Sources & evidence

ORD record
ord-1d9e9251f889489f8f205e420e8713fd
Source dataset
uspto-grants-2006_09
Patent number
US07112698B2

Reaction notes

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