Ethylene Glycol → Acetic acid, 2-chloro-, 1,1'-(1,2-ethanediyl) ester
Reaction equation
[CH2:1]([OH:4])[CH2:2][OH:3].[Cl:5][CH2:6][C:7]([OH:9])=O>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Cl:5][CH2:6][C:7]([O:3][CH2:2][CH2:1][O:4][C:7](=[O:9])[CH2:6][Cl:5])=[O:9]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
In a 2 liter, 4 necked round bottom flask equipped with a mechanical stirrer, a solution of ethylene glycol (100 grams, 1.611 moles), chloroacetic acid (385 grams, 4.031 moles) and para toluenesulphonic acid (1 gram) in toluene (750 ml), was refluxed for 8 hours using a Dean-Stark apparatus. It was then cooled to room temperature. The toluene layer was washed with water (2×300 ml), 5% sodium bicarbonate solution (3×500 ml) and again with water (2×300 ml), dried over sodium sulfate, and distilled to provide crude 1, which was purified by high vacuum distillation to provide pure 1 (242 grams, 69.8%), which slowly crystallized to white crystals. m.p: 44° C., 1H NMR (CDCl3) δ 4.16 (s, 2H, CH2), 4.85 (s, 2H, CH2)