Ethyl vinyl ether → 3-Chloro-2-(1-ethoxyethoxy)propyl acetate

HRID 1075313Notes

Reaction equation

HRID 1075313 reaction equation
[C:1]([O:4][CH2:5][CH:6]([OH:9])[CH2:7][Cl:8])(=[O:3])[CH3:2].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH:22]([O:24][CH2:25][CH3:26])=[CH2:23]>>[C:1]([O:4][CH2:5][CH:6]([O:9][CH:22]([O:24][CH2:25][CH3:26])[CH3:23])[CH2:7][Cl:8])(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 8023Ethyl vinyl etherHCID 980693-Chloro-2-hydroxypropyl acetateHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 131539053-Chloro-2-(1-ethoxyethoxy)propyl acetate

Procedure

To the crude acetate prepared in Example 8 was added 10 g of p-toluenesulfonic acid monohydrate and then dropwise, over a period of 2 hours, 815 g (11.3 moles) of ethyl vinyl ether. The reaction was midly exothermic and the temperature was maintained at 35°-37° C. by occasional cooling. After the addition was complete, the reaction mixture was heated at 35°-40° C. for 16 hours. The crude material was used in the subsequent step.

Workup

  1. temperaturethe temperature was maintained at 35°-37° C. by occasional cooling
  2. additionAfter the addition
  3. temperaturethe reaction mixture was heated at 35°-40° C. for 16 hours

Sources & evidence

ORD record
ord-d24119af085f4d9aab03dc4dddda55de
Source dataset
uspto-grants-1983_07
Patent number
US04395561

Reaction notes

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