Formaldehyde → HCID 54283426, compound

Participants

Reaction Steps

11.0 g of 3-hydroxy-4-methoxyphenylacetic acid is dissolved in 550 ml of benzene and refluxed to remove water as azeotrope. Then, 14.0 g of benzeneboronic acid is added thereto, and refluxed for approximately 1 hour while removing the water produced. (In this reaction, the starting phenylacetic acid works as the carboxylic acid catalyst). At 2-3 hour intervals, each 2-3 g of paraformaldehyde is added while continuing the removal of water, and after the lapse of 9 hours an additional 1.0 g of benzeneboronic acid is added thereto. The reaction is completed within a period of 20 hours, and the solvent is completely distilled off under reduced pressure. The crystalline residue after addition of 150 ml of water is kept on an oil bath at 90°-100° C. for 1.5 hours under stirring. The reaction mixture is cooled to room temperature, and the precipitated crystals are collected and recrystallized from acetone-ether to give 9.70 g (83% yield) of 3-hydroxy-2-hydroxymethyl-4-methoxyphenylacetic acid as the δ-lactone having mp. 183°-185° C. IR νmaxCHCl 3 3540, 1740, 1600, 1277, 1030, 983cm-1. NMR (d6 -DMSO) δ 3.80 (3H. singlet), 3.65 (2H, singlet), 5.32 (2H, singlet), 6.70, 6.90 (AB quartet, J = 8.0 Hz), 8.07 (1H, singlet) ppm. Anal. Aclcd. for C10H10O4 : C, 61.85; H, 5.19 (%). Found: C, 61.70; H, 5.17 (%).

Provenance & Evidence