Benzoic acid, 4-[(4-formyl-2-methoxyphenoxy)methyl]-, methyl ester synthesis

Yield:-

Reaction Conditions:

with potassium carbonate in ethanol;N,N-dimethyl-formamide;Microwave irradiation;Heating;

Steps:

5.1.1. General procedure for the synthesis of intermediates [TFI-1(int)to TFI-11(int)]

General procedure: We adapted methods described in the literature to prepare theintermediate compounds TFI-1(int) to TFI-11(int) by using microwaveassisted synthesis [19e22]. The corresponding benzylbromide (1a-1c; 1 eq.), the hydroxybenzaldehyde (2a-2c; 1 eq.), and K2CO3 (1eq.) were mixed in EtOH (5 mL) inside a microwave reactor vesseland heated to 90 C for 12 h with magnetic stirring. The reactionswere monitored by TLC and, upon completion, the final productsprecipitated as white solid crystals (insoluble in EtOH), which werethen filtered off and washed with hot water (5 mL), followed by asecond washing with hexane (3 mL); after drying the product intermediateswe calculated their purity (about 95%) by 1H and 13CNMR. The overall yields for these reactions was about 80%. IntermediatesTFI-1(int), TFI-3(int) [19,20,22], and TFI-10(int) [21], wereconfirmed by 1H and 13C NMR which were in accordance to thereported analytical data [23].

References:

Tabatabaei Dakhili, Seyed Amirhossein;Pérez, David J.;Gopal, Keshav;Haque, Moinul;Ussher, John R.;Kashfi, Khosrow;Velázquez-Martínez, Carlos A. [European Journal of Medicinal Chemistry,2021,vol. 209,art. no. 112902]