Benzyl Bromide → Phenylmethyl 3-hydroxy-2-(hydroxymethyl)-2-methylpropanoate

Participants

Reaction Conditions

Reaction Steps

A mixture of 2,2-bis(methylol)propionic acid (bisMPA) (18.0 g, 0.134 mol), KOH (85% assay; 8.9 g, 0.135 mol), and DMF (100 mL) was heated to 100° C. for 1 hour (the reaction mixture became a homogenous solution after 0.5 hour reaction). Benzyl bromide (27.6 g, 0.162 mol) was added to the warm solution under stirring, and the reaction was continued at 100° C. for 16 hours. The reaction mixture was cooled down and the solvent was removed under vacuum. Ethyl acetate (120 mL), hexanes (120 mL), and water (80 mL) were added to the residue. The organic layer was retained, washed with water (80 mL), dried over MgSO4 and evaporated. The resulting solid was recrystallized from toluene (30 mL) to give pure benzyl 2,2-bis(methylol)propionate (BnMPA) (19.5 g, 65%). 1H NMR (400 MHz, CDCl3, 22° C.): delta 7.38 (m, 5H, PhH), 5.19 (s, 2H, —OCH2Ph), 3.94 (d, 2H, —CH2OH), 3.73 (d, 2H, —CH2OH), 1.12 (s, 3H, —CH3).

Provenance & Evidence