Hydrochloric Acid → HCID 102004065, compound

Participants

Reaction Steps

To a stirred solution of 7.44 g (0.06 mol) sodium carbonate in 25 ml of water was added 4.76 g (0.02 mol) of 6-bromo-L-ascorbic acid in small portions, followed by 3.8 g (0.04 mol) of phenol. The solution thickened to a white mobile paste, gradually turning yellow after stirring 6 hours under a nitrogen atmosphere. The reaction mixture was then adjusted to pH 0.5 with 6 N aqueous hydrochloric acid the aqueous solution extracted with ethyl acetate (3×100 ml), the ethyl acetate layer washed with water, brine and dried over anhydrous magnesium sulfate. On removal of solvent in vacuo the residue was triturated with benzene, the resulting crystals collected by filtration and dried under vacuum overnight affording 1.54 g of crude title compound. A sample for analysis was obtained by recrystallization from nitromethane followed by drying under vacuum overnight: mp 160°-161°; VmaxKBr 5.68 (s) 6.00 (s); 1H-nmr (D2O): 7.54-6.75 (m, 5, arom.), 4.93 (broad s, l), 7.20 (m, 3, --CH2 --O and --CH--OH); mass spectrum (70 eV): m/e 252.0563 (parent, C12H12O6, 136 (--O--CH2 --C+H--OH), 116 ##STR4## 107 (--O+ =CH2), 94 (base, --OH); [α]D24 79.3° (C 1.09, CH3OH).

Provenance & Evidence