ChemicalBook CAS DataBase List 2'-Methoxycinnamaldehyde

2'-Methoxycinnamaldehyde synthesis

9synthesis methods

Product Name:2'-Methoxycinnamaldehyde
CAS Number:1504-74-1
Molecular formula:C10H10O2
Molecular Weight:162.19

It is formed after a long contact period between salicylaldehyde and acetaldehyde in diluted alkaline solution; it may also be formed by condensation of salicylaldehyde methylether with acetaldehyde under alkaline conditions; from the corresponding oxime. It may be isolated and purified from powdered cinnamon.

1504-61-6 Synthesis

1504-61-6
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1504-74-1
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Yield:1504-74-1 94%

Reaction Conditions:

with 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical;copper diacetate in water;acetonitrile at 20; for 4 h;Green chemistry;

Steps:

General procedure: A mixture of alcohol (5.0 mmol), Cu(OAc)₂ (9.1 mg, 0.05 mmol), and TEMPO (7.8 mg, 0.05 mmol) in CH₃CN/H₂O (5/10 mL) was stirred at room temperature for specified time. After completion of the reaction (monitored by TLC, eluents: petroleum ether/ethyl acetate = 4/1), dichloromethane (10 mL) was added to the resulting mixture. The dichloromethane phase was separated, and the aqueous phase was further extracted with dichloromethane (10 mL × 2). The combined organic layers were dried over anhydrous sodium sulfate and concentrated to give a residue, which was purified by column chromatography (eluents: petroleum ether/ethyl acetate = 10/1) to provide the desired product.

References:

Jiang, Jian-An;Du, Jia-Lei;Wang, Zhan-Guo;Zhang, Zhong-Nan;Xu, Xi;Zheng, Gan-Lin;Ji, Ya-Fei [Tetrahedron Letters,2014,vol. 55,# 10,p. 1677 - 1681] Location in patent:supporting information

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33538-83-9 Synthesis