4'-Hydroxyacetophenone → Benzyl [2-(4-acetylphenoxy)ethyl]carbamate

HRID 653584Notes

Reaction equation

HRID 653584 reaction equation
C1(C)C=CC(S([O:10][CH2:11][CH2:12][NH:13][C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])(=O)=O)=CC=1.O[C:26]1[CH:31]=[CH:30][C:29]([C:32](=[O:34])[CH3:33])=[CH:28][CH:27]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:17]([O:16][C:14]([NH:13][CH2:12][CH2:11][O:10][C:26]1[CH:31]=[CH:30][C:29]([C:32](=[O:34])[CH3:33])=[CH:28][CH:27]=1)=[O:15])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 74694'-HydroxyacetophenoneHCID 11430Potassium CarbonateHCID 104979822-(Benzyloxycarbonylamino)ethyl 4-methylbenzenesulfonate

Product 1

HCID 19889128Benzyl [2-(4-acetylphenoxy)ethyl]carbamateYield 88.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 35 g of 2-(N-benzyloxycarbonylamino)ethyl p-toluenesulfonate, 13 g of 4'-hydroxyacetophenone and 55 g of anhydrous potassium carbonate in 450 ml of dry acetone was refluxed with stirring for 24 hrs under argon atmosphere. After cooling, the insoluble material was removed by filtration and the filtrate was evaporated. The residue was diluted with ethyl acetate, washed with water, 1% NaOH and brine, dried over anhydrous sodium sulfate, and evaporated under reduced pressure to give a solid, which was recrystallized from hexane-benzene to give 26.5 g of 4'-(2-(N-benzyloxycarbonylamino)ethoxy)-acetophenone as white needles.

Workup

  1. temperaturewas refluxed
  2. temperatureAfter cooling
  3. customthe insoluble material was removed by filtration
  4. customthe filtrate was evaporated
  5. additionThe residue was diluted with ethyl acetate
  6. washwashed with water, 1% NaOH and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customevaporated under reduced pressure
  9. customto give a solid, which
  10. customwas recrystallized from hexane-benzene

Sources & evidence

ORD record
ord-76e7c57116014f118af5bf69da84a97b
Source dataset
uspto-grants-1992_07
Patent number
US05128069

Reaction notes

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