Epichlorohydrin → Allyl 3-chloro-2-hydroxypropyl ether

HRID 1649572Notes

Reaction equation

HRID 1649572 reaction equation
[CH2:1]([OH:4])[CH:2]=[CH2:3].[CH2:5]([CH:7]1[O:9][CH2:8]1)[Cl:6]>[Ag]>[Cl:6][CH2:5][CH:7]([OH:9])[CH2:8][O:4][CH2:1][CH:2]=[CH2:3]

Participants

4

Conditions

Temperature
60 °C

Procedure

A mixture of 87 grams (1.5 mols) of allyl alcohol and 1 milliliter of boron trifluoride-diethyl etherate is heated to 60° C. in a reaction vessel provided with reflux condenser, thermometer and dropping funnel. Within 45 minutes, 46.25 grams (0.5 mol) of epichlorohydrin are constantly added to said mixture. The reaction is exothermic. Thereafter the reaction mixture is rectified via a 40 centimeter silver-coated column, whereupon at first 55 grams of unreacted allyl alcohol are distilled off at 24° C. and a pressure of 15 millibars. By subsequent distillation at 0.08 millibars there are obtained 59.7 grams (79.3% of the theory) of (3-chloro-2-hydroxy-propyl)-allyl ether with a boiling point of 57° C. and a refractive index nD20 =1.4630.

Workup

  1. customprovided
  2. temperaturewith reflux condenser
  3. distillationare distilled off at 24° C.
  4. distillationBy subsequent distillation at 0.08 millibars

Sources & evidence

ORD record
ord-73ea6a32ceba41278f66a6e25e3940a1
Source dataset
uspto-grants-1983_11
Patent number
US04418207

Reaction notes

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