Ethylene chlorohydrins
Ethylene chlorohydrins
Ethylene chlorohydrins
or β-chloroethyl alcohol or 2-chloroethanol is a colorless liquid, b.p. 128oC. It
is very useful in organic syntheses since it contains two different reactive
groups; e.g., by heating with aqueous sodium cyanide it may be converted into
ethylene cyanohydrins, which, on hydrolysis, gives β-hydroxypropionic acid.
HOCH2CH2Cl + NaCN
⟶ HOCH2CH2CN + NaCl (79-80%)
HOCH2CH2CH (HCl) ⟶ HOCH2CH2CO2H
When glycol
is treated with phosphorus trichloride or phosphorus tribromide, the corresponding
ethylene dihalide is obtained:
Phosphorus tri-iodide,
however, produces ethylene. Ethylene di-iodide is formed as an inter mediate, but
readily eliminates iodine:
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