ChemicalBook CAS DataBase List (2-Methoxyethyl)benzene

(2-Methoxyethyl)benzene synthesis

14synthesis methods

Product Name:(2-Methoxyethyl)benzene
CAS Number:3558-60-9
Molecular formula:C9H12O
Molecular Weight:136.19

By catalytic reduction of phenylacetaldehyde dimethyl acetal; from phenylethyl alcohol and methanol

122-78-1
334 suppliers
$10.00/5g

149-73-5 Synthesis

149-73-5
548 suppliers
$12.00/5g

3558-60-9
121 suppliers
$29.00/25ml

Yield:3558-60-9 66.5%

Reaction Conditions:

with 5%-palladium/activated carbon;hydrogen;toluene-4-sulfonic acid in methanol at 130; under 22502.3 Torr; for 6 h;Autoclave;Inert atmosphere;

Steps:

3 Synthesis of 2-methoxyethylbenzene
2.40 g (20.0 mmol) of 2-phenylacetaldehyde, 4.25 g (40.0 mmol) of methyl orthoformate, 2.4 ml of methanol,12.0 mg of p-toluenesulfonic acid monohydrate, and 60.0 mg of 5% palladium carbon were added into a 100 ml autoclave(using an inner tube). After the inside of the system was substituted with nitrogen, substitution with hydrogen wasperformed and 3.0 MPa of hydrogen gas was enclosed. The temperature in the autoclave was controlled to 130°C andstirring was continued for 6 hours. After the stirring, the reaction solution was cooled and then the hydrogen gas waspurged. Thereafter, the palladium catalyst was removed by filtration operation, and methanol and excess methyl ortho-formate were collected under normal pressure to thereby obtain 2.82 g (value at internal standard quantitative determi-nation: 64.2 wt%, yield: 66.5%) of 2-methoxyethylbenzene.1H-NMR (CDCl3): σ = 2.89 (2H, t), 3.38 (3H, s), 3.58 (2H, t), 7.19-7.27 (5H, m)

References:

Takasago International Corporation;KOMATSUKI Yasuhiro;ISHIDA Kenya;YAGI Kenji EP2813482, 2014, A1 Location in patent:Paragraph 0141

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60-12-8 Synthesis