ChemicalBook CAS DataBase List 2',4',6'-TRIMETHOXYACETOPHENONE

2',4',6'-TRIMETHOXYACETOPHENONE synthesis

13synthesis methods

Product Name:2',4',6'-TRIMETHOXYACETOPHENONE
CAS Number:832-58-6
Molecular formula:C11H14O4
Molecular Weight:210.23

Preparation by reaction of dimethyl sulfate with phloroacetophenone.

621-23-8 Synthesis

621-23-8
485 suppliers
$7.00/5g

75-36-5 Synthesis

75-36-5
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$17.92/100G

832-58-6
143 suppliers
$11.00/250mg

Yield: 99%

Reaction Conditions:

Stage #1:1,2,3-trimethoxybenzene in dichloromethane at 0; for 0.166667 h;
Stage #2:acetyl chloride with aluminum (III) chloride in dichloromethane for 2 h;Friedel-Crafts Acylation;

Steps:

2,4,6-Trimethoxyacetylbenzene (8)
A solution of 7 (2.0 g, 11.8 mmol) in CH₂Cl₂ was cooled down to 0 °C for 10 min, and then added AlCl₃ (1.9 g, 14.2 mmol) and acetyl chloride (1.26 mL, 1.4 g, 17.7 mmol). After stirring 2 h, the reaction mixture was cooled and quenched by adding a solution of 10% NaOH (aq) (40 mL), and extracted by CH₂Cl₂ (330 mL). The organiclayer was washed with brine, dried over Na₂SO₄, and concentrated in vacuo. The residue was subjected to column chromatography (Silica gel, hexane/EA 5:1) to provide 8 (2.5 g, 99%) as a white solid:mp 103-106 °C (lit.⁹ 101-103 °C). IR (neat): ν 3373, 2977, 1692,1602, 1415, 1210, 1130, 818 cm^-¹; ¹H NMR (400 MHz, CDCl₃): δ 6.09 (s, 2H, Ar-H), 3.81 (s, 3H, OCH3), 3.78 (s, 6H, 2 x OCH₃), 2.47 (s, 3H,CH₃CO-).