5-(3-METHYL-4-NITRO-PHENOXYMETHYL)-FURAN-2-CARBALDEHYDE synthesis

Yield: 83%

Reaction Conditions:

with potassium carbonate in N,N-dimethyl-formamide;acetonitrileReflux;

Steps:

5-Aryloxymethylfurfurals 8a,b (general procedure).
General procedure: A mixture of 5-chloromethylfurfural³⁶ (0.010 mol), the corresponding phenol (0.011 mol), and potassium carbonate (2.00 g, 0.0145 mol)in a mixture of acetonitrile-DMF (20 mL, 9 : 1, v/v) was refluxed for 5-6 h with stirring (TLC monitoring). After evaporation of the solvents, the residue was treated with water, a precipitate formed was filtered off, washed with 30% aqueous methanol, and dried in air. Yields and physicochemical characteristics of aldehydes 8a,b are given in Table 4. 5-[(3-Methyl-4-nitrophenoxy)methyl]-2-furancarbaldehyde (8b). MS (EI, 70 eV), m/z (Irel (%)): 261 [M]+ (2), 109 [5CHOfuryl2CH2]+ (100). 13C NMR (DMSOd6), : 20.61 (C(7)),62.11 (C(8)), 113.06 (C(3)Ar), 113.24 (C(10)), 118.22 (C(5)Ar),123.67 (C(11)), 127.26 (C(6)Ar), 136.39 (C(2)Ar), 142.23 (C(1)Ar),152.58 (C(12)), 155.18 (C(9)), 161.05 (C(4)Ar), 178.54 (CHO).IR (KBr), /cm-1: 3112 (C-H of furan), 2869 (C-H), 1678(C=O), 1606-1588 (C=C), 1504 (C-N=O), 1490-1459 (CH3,CH2), 1333 (NO2), 1249 (C-O-C), 1192-1074 (furan), 1025(C-O-C).

References:

Khachatryan;Razinov;Kolotaev;Belus̈;Matevosyan [Russian Chemical Bulletin,2015,vol. 64,# 2,p. 395 - 404][Izv. Akad. Nauk, Ser. Khim.,2015,# 2,p. 395 - 404,10]