3',4',5'-Trimethoxyacetophenone → HCID 5379234, compound

HRID 2217066Notes

Reaction equation

HRID 2217066 reaction equation
[CH2:1]([O:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1)[CH3:2].[CH3:12][C:13]([C:15]1[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=1)=[O:14].[OH-].[Na+]>CO>[CH2:1]([O:3][C:4]1[CH:11]=[CH:10][C:7](/[CH:8]=[CH:12]/[C:13]([C:15]2[CH:16]=[C:17]([O:25][CH3:26])[C:18]([O:23][CH3:24])=[C:19]([O:21][CH3:22])[CH:20]=2)=[O:14])=[CH:6][CH:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 143453',4',5'-TrimethoxyacetophenoneHCID 14798Sodium HydroxideHCID 248344-Ethoxybenzaldehyde

Product 1

HCID 5379234HCID 5379234, compoundYield 55.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 4-ethoxybenzaldehyde (1.32 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. 1.8 g (55%) of a pale yellow powder was isolated. 1H-NMR (CDCl3) δ 7.8 (d, 1H), 7.6 (d, 2H), 7.3 (d, 1H), 6.9 (d, 2H), 4.1 (q, 2H), 3.9 (s×2, 9H), 1.4 (t, 3H). 13C-NMR (CDCl3) δ 189.2, 161.1, 153.1, 142.3, 133.8, 127.4, 63.4. Mass Spectrum m/e (M+1) 343.

Workup

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

Sources & evidence

ORD record
ord-3a6ef8817da64f1bb84965a2d8e8de6d
Source dataset
uspto-grants-2006_09
Patent number
US07112698B2

Reaction notes

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