Benzene → 1-[4-(2-Chloroethoxy)phenyl]ethanone

HRID 1721949Notes

Reaction equation

HRID 1721949 reaction equation
[OH-:1].[Na+].[CH:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C1(C)C=CC(S([O:18][CH2:19][CH2:20][Cl:21])(=O)=O)=CC=1.[C:23](#N)[CH3:24]>>[Cl:21][CH2:20][CH2:19][O:18][C:3]1[CH:8]=[CH:7][C:6]([C:23](=[O:1])[CH3:24])=[CH:5][CH:4]=1

Participants

5

Reactant 4

HCID 241BenzeneHCID 6342AcetonitrileHCID 6639Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate)HCID 14798Sodium Hydroxide

Product 1

HCID 136911911-[4-(2-Chloroethoxy)phenyl]ethanone

Procedure

A mixture of 100 mg of 4-hydroxy-acetophenone, 96 mg of n-tetrabutylammonium acid sulfate, 1.5 ml of 50% sodium hydroxide solution, 3 ml of benzene, 1.5 ml of acetonitrile and 0.2 ml of 2-chloroethyl p-toluene sulfonate was refluxed for 18 hours under an inert atmosphere and the decanted phase was extracted with benzene. The organic phase was washed with water, dried over a deshydrant and evaporated to dryness under reduced pressure. The residue was chromatographed over silica and eluted with dichloroethane to obtain 127 mg of 1-[4-(2-chloroethoxy)-phenyl]-ethanone melting at ≃62° C.

Workup

  1. temperaturewas refluxed for 18 hours under an inert atmosphere
  2. extractionthe decanted phase was extracted with benzene
  3. washThe organic phase was washed with water
  4. customdried over a deshydrant
  5. customevaporated to dryness under reduced pressure
  6. customThe residue was chromatographed over silica
  7. washeluted with dichloroethane

Sources & evidence

ORD record
ord-8c0c92375b5742e8bada3c2335641388
Source dataset
uspto-grants-1989_08
Patent number
US04853408

Reaction notes

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