ChemicalBook CAS DataBase List 2,5-DIMETHOXY-4-METHYLBENZALDEHYDE

2,5-DIMETHOXY-4-METHYLBENZALDEHYDE synthesis

6synthesis methods

Product Name:2,5-DIMETHOXY-4-METHYLBENZALDEHYDE
CAS Number:4925-88-6
Molecular formula:C10H12O3
Molecular Weight:180.2

2,5-Dimethoxy-4-methylbenzaldehyde is used in the preparation of phenylamine derivative as potential psychotomimetics. It was prepared from N-methyifor maniiide, phosphorus oxytrichio ride and 2,5-dimethoxytoiuene heated for 6 hours at 50℃.

24599-58-4
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$15.00/1g

93-61-8
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4925-88-6
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$42.39/1g

Yield:4925-88-6 67%

Reaction Conditions:

Stage #1:N-methyl-N-phenylformamide with trichlorophosphate at 20; for 0.666667 h;
Stage #2:2,5-dimethoxy toluene at 50; for 6 h;
Stage #3: with sodium acetate;sodium hydrogensulfitemore than 3 stages;

Steps:

A.a Preparation of the Syntetic Intermediates; A. Preparation of the Acids 1 (Variants); 2,5-Dimethoxy-4-methylbenzoic Acid (Compound A.1); a) 2,5-Dimethoxy-4-methylbenzaldehyde
After stirring a mixture of 8.5 mi of N-methyifor maniiide (0.068 moi) and 6.3 mi of phosphorus oxytrichio ride (0.068 moi) at room temperature for 40 minutes, 17.8 g of 2,5-dimethoxytoiuene (0.117 moi) are introduced. The reaction mixture is heated for 6 hours at 500 C. and then, after returning to a temperature of 20 C., it is hydroiysed with 100 mi of aqueous 10% sodium acetate soiution, extracted twice with diethyi ether and concentrated. The residue is taken up in aqueous sodium hydrogen suiphite soiution and extracted twice with diethyi ether. The aqueous phase is basied (pH=12) in order to give white crystais; m.p.=83 C.; yieid=67%.

References:

Bignon, Eric;Bras, Jean Pierre;De Cointet, Paul;Despeyroux, Pierre;Frehel, Daniel;Gully, Danielle US2004/43995, 2004, A1 Location in patent:Page 12

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4885-02-3 Synthesis