(4-Methoxy-3,5-dimethylphenyl)acetic acid synthesis

5synthesis methods

Product Name:(4-Methoxy-3,5-dimethylphenyl)acetic acid
CAS Number:104216-50-4
Molecular formula:C11H14O3
Molecular Weight:194.23

Propanedioic acid, 2-(4-methoxy-3,5-dimethylphenyl)-, 1,3-diethyl ester

4503-91-7
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(4-Methoxy-3,5-dimethylphenyl)acetic acid

104216-50-4
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$240.00/1g

Yield:104216-50-4 32%

Reaction Conditions:

Stage #1: <3,5-Dimethyl-4-methoxy-phenyl>-malonsaeure-diethylesterwith water;sodium hydroxide in tetrahydrofuran; for 3 h;Reflux;
Stage #2: with hydrogenchloride in tetrahydrofuran at 20; pH=1; for 4 h;

Steps:

6.6.2.b

The malonic acid diethyl ester (0.34 mmol, 0.1 g) obtained was then dissolved in 2 N NaOH /THF:H₂O (1:1) (350 μL) and refluxed for 3 h. After acidifying the reaction mixture to pH 1 using cone. HCI, the mixture was stirred for a further hour at room temperature. The solution was then set to pH 13 using 1 N NaOH and extracted with diethyl ether (20 ml). The aqueous phase was set to pH 5 using 1 N HCI and extracted with EE (3 x 20 ml). The combined organic phases were washed with sat. NaCI solution, dried over magnesium sulphate and filtered. After removal of the solvent under vacuum, 0.021 g (32 % yield) of the desired 2-(4-methoxy-3,5-dimethylphenyl)acetic acid could be obtained.

References:

WO2010/127856,2010,A1 Location in patent:Page/Page column 83; 84

576-26-1 Synthesis