Synthesis of bis-(3-chloro-2-hydroxypropyl) ether

Preparation of bis-(3-chloro-2-hydroxypropyl) ether

Alternative Names: 1,1′-Oxybis(3-chloropropane-2-ol);

Preparation of bis-(3-chloro-2-hydroxypropyl) ether

Preparation of bis-(3-chloro-2-hydroxypropyl) ether

Carbon dioxide is led into a mixture of 0.25 mole of diallyl ether, 2.5 liters of water, and 102 g (0.25 mole) 35% of calcium hypochlorite solution  at 3° C with stirring and cooling. A dry-ice condenser is placed on the reaction flask to prevent loss of diallyl ether. The calcium hypochlorite is consumed in 2 hours, then 51 g additionally are added and carbon dioxide is passed in with stirring for a further 2 hours. The solution is filtered from calcium carbonate, saturated with sodium chloride, and extracted with ether. The yield is 94.4% and the b.p. is 150-165° C/3 mmHg or, after a further distillation 138-139° C/1 mmHg.

J. Amer. Chem. Soc, 71, 2667 (1949).

IUPAC Name

1-chloro-3-(3-chloro-2-hydroxypropoxy)propan-2-ol

InChI

InChI=1S/C6H12Cl2O3/c7-1-5(9)3-11-4-6(10)2-8/h5-6,9-10H,1-4H2

InChI Key

XAZDZMUGHYYPQM-UHFFFAOYSA-N

Canonical SMILES

C(C(CCl)O)OCC(CCl)O

Depositor-Supplied Synonyms

SCHEMBL202567, 1,1′-Oxybis(3-chloropropane-2-ol)

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