[OH:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6]([OH:10])[C:7]([OH:9])=[O:8])=[CH:4][CH:3]=1.[Na].[CH2:14]1[O:16][CH2:15]1.Cl>[OH-].[Na+].O>[OH:16][CH2:15][CH2:14][O:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6]([OH:10])[C:7]([OH:9])=[O:8])=[CH:4][CH:3]=11040.8 g (5.00 mol) of 4-hydroxymandelic acid, sodium salt monohydrate, 10.0 g (0.25 mol) of sodium hydroxide and 1000 ml of water are placed in an autoclave of 6.3 liter capacity. The autoclave is flushed with nitrogen and 330.4 g (7.50 mol) of ethylene oxide are then injected. The contents are slowly heated to 95° C. over a period of 2 hours with stirring and stirred at this temperature for another 2 hours. The still hot reaction mixture is poured into another vessel, acidified at 95° C. with 540 ml (about 5.5 mol) of 32% hydrochloric acid and crystallized by slow cooling to about +10° C. The precipitated product is filtered with 1000 ml of cold water and dried to give 948 g (89%) of 4-(2-hydroxyethoxy)mandelic acid, m.p. 162°-164° C. (compound (201), Table 2).
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