Epichlorohydrin → 1-(2,3-Epoxypropoxy)-4-(2-hydroxyethoxy)benzene

HRID 4557

Reaction equation

HRID 4557 reaction equation
[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.[CH2:12]([CH:14]1[O:16][CH2:15]1)Cl.C(=O)([O-])[O-].[K+].[K+]>>[O:16]1[CH2:15][CH:14]1[CH2:12][O:11][C:8]1[CH:7]=[CH:6][C:5]([O:4][CH2:3][CH2:2][OH:1])=[CH:10][CH:9]=1

Participants

4

Reactant 3

HCID 7835EpichlorohydrinHCID 11430Potassium CarbonateHCID 98340144-(2-Hydroxyethoxy)phenol

Product 1

HCID 201513091-(2,3-Epoxypropoxy)-4-(2-hydroxyethoxy)benzene

Procedure

With stirring, 13 g of crude 4-(2-hydroxyethoxy)phenol, 35 m of epichlorohydrin and 23.5 g of potassium carbonate are heated for 11/2 hours to reflux temperature. The reaction mixture is filtered and the filtrate is concentrated by evaporation under reduced pressure. The residual oil gradually congeals to a crystalline solid, which is recrystallised from isopropanol, affording 1-(2,3-epoxypropoxy)-4-(2-hydroxyethoxy)benzene with a melting point of 65°-67° C. Working up of the mother liquor yields further crystalline product.

Workup

  1. temperatureto reflux temperature
  2. filtrationThe reaction mixture is filtered
  3. concentrationthe filtrate is concentrated by evaporation under reduced pressure
  4. customis recrystallised from isopropanol

Sources & evidence

ORD record
ord-74326da63a1b43b7b1f17eec13973a19
Source dataset
uspto-grants-1988_02
Patent number
US04727067

Linked notes

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