Diethyl Ether → 2-(9-Anthryloxy)ethyl chloride

HRID 414475

Reaction equation

HRID 414475 reaction equation
[Cl:1][CH2:2][CH2:3]OS(C1C=CC(C)=CC=1)(=O)=O.[CH:15]1[C:28]2[C:27](=[O:29])[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:20][C:19]=2[CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].CCOCC>CN(C)C=O>[CH:25]1[C:26]2[C:21](=[CH:20][C:19]3[C:28]([C:27]=2[O:29][CH2:3][CH2:2][Cl:1])=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6639Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate)HCID 7018AnthroneHCID 11430Potassium Carbonate

Product 1

HCID 212808202-(9-Anthryloxy)ethyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

2-Chloroethyl-p-toluenesulphonate (6.0 g) was added to a mixture of anthrone (5 g) and potassium carbonate (5 g) in dimethylformamide (130 ml). After stirring for 24 hours at 70° C., the reaction mixture was added to ether. The resultant solution was washed with dilute aqueous potassium hydroxide, dried with magnesium sulphate, and evaporated to yield a crude product which was chromatographed on silica gel, eluting with 4:1 hexane:ethyl acetate, to give 2-(9-anthryloxy)ethyl chloride.

Workup

  1. washThe resultant solution was washed with dilute aqueous potassium hydroxide
  2. dry with materialdried with magnesium sulphate
  3. customevaporated
  4. customto yield a crude product which
  5. customwas chromatographed on silica gel
  6. washeluting with 4:1 hexane

Sources & evidence

ORD record
ord-7d3e334ef5db49c9af058e06e27c9fef
Source dataset
uspto-grants-1988_12
Patent number
US04792551

Linked notes

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