Ethanol → 2,3-Bis(benzyloxy)benzene-1,4-dicarboxylic acid

Participants

Reaction Conditions

Reaction Steps

2 (56.970 g, 0.102 mol) was dissolved in 200 mL 1:1:EtOH:dioxane in a 1-L round-bottom flask, resulting in a dark orange, clear solution, to which a suspension of LiOH (7.315 g, 0.305 mol) in 75 mL water was added. The flask was fitted with a reflux condenser and magnetically stirred. The emulsion (containing undissolved LiOH) was heated to 60° C. for 12 h, and became a translucent, orange solution. The reaction mixture was filtered through a M glass frit, dissolved in 500 mL basic water, and washed with DCM (3×250 mL). The aqueous layer was acidifed with ˜80 mL conc. HCl, and the resulting white precipitate was filtered and washed with water. The solid was dried using house vacuum overnight, ground into a white powder, and dried on the vacuum line for 12 h (100%).

Provenance & Evidence