Catechol → HCID 21490506, compound

HRID 1973768Notes

Reaction equation

HRID 1973768 reaction equation
[CH2:1]([CH:3]1[O:5][CH2:4]1)[Cl:2].[C:6]1([C:8](=[CH:10][CH:11]=[CH:12][CH:13]=1)[OH:9])[OH:7].[OH-:14].[Na+]>O>[C:8]1([O:9][CH2:4][CH:3]([OH:5])[CH2:1][Cl:2])[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=1[O:7][CH2:4][CH:3]([OH:14])[CH2:1][Cl:2]

Participants

5

Reactant 3

HCID 289Catechol2×HCID 7835EpichlorohydrinHCID 14798Sodium Hydroxide

Product 1

HCID 21490506HCID 21490506, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 962WaterCatalyst

Conditions

Temperature
40 °C

Procedure

37.0 g. of epichlorohydrin are added under a nitrogen atmosphere to 11.0 g. of catechol. After the catechol is dissolved, a solution of 0.15 g of sodium hydroxide in a few drops of water is added dropwise and the temperature is raised to 40° C. At this temperature the reaction mixture is stirred for 48 hours, after which the remaining epichlorohydrin is distilled off under reduced pressure. The resulting oil is dissolved in chloroform, washed twice with water and distilled. 19.5 g. of 1,1'-(o-phenylenedioxy)-bis-(3-chloropropan-2-ol) are obtained with a boiling point of 153°-156° C./10-2 -10-3 mm.Hg. After crystallization from diethyl ether the melting point is 64°-66° C.

Workup

  1. distillationafter which the remaining epichlorohydrin is distilled off under reduced pressure
  2. dissolutionThe resulting oil is dissolved in chloroform
  3. washwashed twice with water
  4. distillationdistilled

Sources & evidence

ORD record
ord-b2edba7ee93a4b26abb3da3a500b85f7
Source dataset
uspto-grants-1976_12
Patent number
US03998874

Reaction notes

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