The Duff reaction is commonly used to introduce a formyl group to an aromatic ring with hexamethylenetetramine (HMTA) as the carbon source. The purpose of this project is to efficiently produce mono- and dialdehydes by the Duff reaction from substituted phenols under microwave irradiation. The reaction was performed in a sealed tube placed in a CEM microwave reactor and identification of the products was completed using NMR. The substituents of the phenols tested varied from the highly electron donating methoxy group to the highly electron withdrawing nitro group. Monoaldehyde formation with 4-methoxyphenol and 4-t-butylphenol produced high yields with only five minutes in the reactor. Monoaldehyde formation wtih 4-nitrophenol had yields of 56% and 57% for five and 15 minutes in the reactor. The dialdehyde formation reactions were done in the presence of a large excess of HMTA and reactions with 4-methoxyphenol produced a mixture of the mono- and dialdehyde. The results of the reaction using a large variety of starting materials will be presented. Monoaldehyde formation via the Duff reaction in the microwave reactor is very successful while the dialdehyde formation is more difficult.

Formylation of substituted phenols using mIcrowave irradiation

249th National Meeting (2015)

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