1-Bromo-2-Chloroethane → HCID 20369773, compound

HRID 616343Notes

Reaction equation

HRID 616343 reaction equation
O[CH2:2][CH2:3][O:4][C:5]1[CH:18]=[CH:17][C:16]2[C:15](=[O:19])[C:14]3[C:9](=[CH:10][CH:11]=[C:12]([O:20]CCO)[CH:13]=3)[C:8](=[O:24])[C:7]=2[CH:6]=1.BrCCO.Br[CH2:30][CH2:31][Cl:32].S(Cl)([Cl:35])=O>C(Cl)(Cl)Cl.N1C=CC=CC=1>[Cl:32][CH2:31][CH2:30][O:20][C:12]1[CH:11]=[CH:10][C:9]2[C:8](=[O:24])[C:7]3[C:16](=[CH:17][CH:18]=[C:5]([O:4][CH2:3][CH2:2][Cl:35])[CH:6]=3)[C:15](=[O:19])[C:14]=2[CH:13]=1

Participants

7

Reactant 4

HCID 78491-Bromo-2-ChloroethaneHCID 108982-BromoethanolHCID 24386Thionyl ChlorideHCID 10969503HCID 10969503, compound2×

Product 1

HCID 20369773HCID 20369773, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6212ChloroformSolvent

Procedure

2,6-Bis(2-hydroxyethoxy)anthraquinone can be prepared as in (A) above by substituting 75 g. (0.60 mole) of 2-bromoethanol for 1-bromo-2-chloroethane. Then, with stirring, 25 g. of thionyl chloride is added to a mixture of 20 g. (0.06 mole) of the 2,6-bis(2-hydroxyethoxy)anthraquinone and 0.5 ml. of pyridine in 200 ml. of chloroform. The mixture is heated to reflux on a steam bath for six hours, after which the excess thionyl chloride and chloroform are removed under reduced pressure. The residue is dissolved in chloroform and the solution washed with saturated sodium bicarbonate solution and water, then dried with anhydrous magnesium sulfate. As in (A) above, the 2,6-bis(2-chloroethoxy) anthraquinone is isolated and recrystallized, if needed.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux on a steam bath for six hours
  3. customafter which the excess thionyl chloride and chloroform are removed under reduced pressure
  4. dissolutionThe residue is dissolved in chloroform
  5. washthe solution washed with saturated sodium bicarbonate solution and water
  6. dry with materialdried with anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-fd0b2c0a7f34489384e21dc7773f233c
Source dataset
uspto-grants-1978_02
Patent number
US04073904

Reaction notes

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