Lactic Acid → 2-Propynyl 2-hydroxypropionate
Reaction equation
[OH:1][CH:2]([CH3:6])[C:3]([OH:5])=[O:4].[CH2:7](O)[C:8]#[CH:9].S(=O)(=O)(O)O.C([O-])(=O)C.[Na+]>C1(C)C=CC=CC=1>[OH:1][CH:2]([CH3:6])[C:3]([O:5][CH2:9][C:8]#[CH:7])=[O:4]Participants
6
[OH:1][CH:2]([CH3:6])[C:3]([OH:5])=[O:4].[CH2:7](O)[C:8]#[CH:9].S(=O)(=O)(O)O.C([O-])(=O)C.[Na+]>C1(C)C=CC=CC=1>[OH:1][CH:2]([CH3:6])[C:3]([O:5][CH2:9][C:8]#[CH:7])=[O:4]52.99 g (0.50 mol) of an aqueous solution of 85% 2-hydroxypropionic acid and 45 mL of toluene were dissolved in 84.09 g (1.50 mol) of propargyl alcohol, and 1.0 mL of concentrated sulfuric acid was added thereto. Using a Dean-Stark device under normal pressure, the formed water was removed from the system, and this was further reacted under reflux under normal pressure. After 3 hours, the reaction liquid was analyzed through liquid chromatography, and the disappearance of the starting materials was confirmed. Then, the reaction liquid was neutralized with sodium acetate added thereto, filtered, and the filtrate was concentrated. The residue was purified through reduced pressure distillation to give 28.81 g (45% yield) of 2-propynyl 2-hydroxypropionate.
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