Ethylene Glycol → 2-((2-Hydroxyethoxy)methyl)anthracene-9,10-dione

HRID 1722205Notes

Reaction equation

HRID 1722205 reaction equation
Cl[CH2:2][C:3]1[CH:16]=[CH:15][C:14]2[C:13](=[O:17])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6](=[O:18])[C:5]=2[CH:4]=1.[CH2:19]([OH:22])[CH2:20][OH:21]>C(Cl)(Cl)Cl>[OH:21][CH2:20][CH2:19][O:22][CH2:2][C:3]1[CH:16]=[CH:15][C:14]2[C:13](=[O:17])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6](=[O:18])[C:5]=2[CH:4]=1

Participants

4

Reactant 2

HCID 174Ethylene GlycolHCID 3443112-(Chloromethyl)anthraquinone

Product 1

HCID 230517302-((2-Hydroxyethoxy)methyl)anthracene-9,10-dione

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
160 °C

Procedure

A suspension of 10.14 g of 2-chloromethylanthraquinone in 50 ml of ethylene glycol is stirred for 14 hours at 160° C. It is taken up in chloroform and the resulting solution is washed with water and saturated sodium chloride solution. Crystallization of the residue of the organic phase (12 g) from toluene gives 9.0 g of 2-(2'-hydroxyethoxy)methylanthraquinone with an m.p. of 129°-130° C.

Workup

  1. washthe resulting solution is washed with water and saturated sodium chloride solution
  2. customCrystallization of the residue of the organic phase (12 g) from toluene

Sources & evidence

ORD record
ord-46ebfe624d48414ba0d0b5bb0c24c93d
Source dataset
uspto-grants-1989_08
Patent number
US04855084

Reaction notes

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