Catechol → Ethylene Oxide

HRID 614296Notes

Reaction equation

[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4])[OH:2].[OH-].[Na+].[CH2:11]1[O:13][CH2:12]1>>[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4])[OH:2].[CH2:12]1[O:13][CH2:11]1.[CH2:5]1[O:4][CH2:3]1

Participants

Reactant 3

HCID 289Catechol

HCID 6354Ethylene Oxide

HCID 14798Sodium Hydroxide

Product 2

HCID 6354Ethylene Oxide

HCID 86736395HCID 86736395, compound

Procedure

In the same manner as in Example 1, 206 parts of catechol and 1.1 parts of sodium hydroxide were reacted with 494 parts of ethylene oxide at not higher than 5 kg/cm2, at 120°-150° C. for 40 minutes thereby to obtain a catechol-ethylene oxide adduct (the average amount of ethylene oxide, n=3) which was a light-yellow viscous liquid. In the same manner as in Example 1, 72.2 parts of the adduct so obtained, 27.8 parts of acrylic acid, 0.1 part of hydroquinone, 1.0 part of p-toluenesulfonic acid and 10.0 parts of benzene were reacted together at 90°-110° C. for 9 hours to produce a reaction mixture having an acid value of 3.9. The reaction mixture so produced was then heated to 110°-120° C. for two hours to remove the benzene therefrom thereby obtaining a light-yellow liquid (y=2).

Sources & evidence

ORD record: ord-b57ff089f7564156acb4fbbb6a8300f8
Source dataset: uspto-grants-1979_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04144283

Reaction notes

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