4'-Hydroxyacetophenone → HCID 70373091, compound

HRID 2165943Notes

Reaction equation

HRID 2165943 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:18][CH2:19][CH2:20][C:21]([CH3:28])([CH3:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23]>C(O)C>[C:8]([C:5]1[CH:6]=[CH:7][C:2]([O:1][CH:20]([CH2:19][CH3:18])[C:21]([CH3:28])([CH3:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:3][CH:4]=1)(=[O:10])[CH3:9]

Participants

5

Reactant 3

HCID 74694'-HydroxyacetophenoneHCID 11430Potassium CarbonateHCID 10681333Ethyl 5-bromo-2,2-dimethylpentanoate

Product 1

HCID 70373091HCID 70373091, compoundYield 65.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 30 g of p-hydroxyacetophenone and 30 g of potassium carbonate was stirred in 500 ml of ethanol at 60° C. for 30 minutes. After cooling to room temperature, 52 g of ethyl 5-bromo-2,2-dimethylpentanoate was added to the reaction mixture. The resulting mixture was heated under reflux overnight while stirring. The solvent was removed from the reaction mixture by distillation and, 500 ml of chloroform and 300 ml of a 5% aqueous hydrogen sodium carbonate solution were added to the residue. After stirring the mixture, the chloroform layer was fractionated and washed successively with water and then with a saturated aqueous sodium chloride solution followed by drying over anhydrous sodium sulfate. Removal of chloroform by distillation gave a residual oily substance. The oily substance was subjected to silica gel column chromatography and eluted using chloroform as an eluant to give 42 g of ethyl p-acetylphenoxy-2,2-dimethylpentanoate as an oily substance. The thus obtained oily substance was dissolved in 1.6 l. of anhydrous methylene chloride and 24 g of bromine was dropwise added to the solution under ice cooling while stirring to allow to react for 3 hours. To the reaction mixture was added 1 liter of ice water. After thoroughly stirring, the organic layer was successively washed with water and with a saturated aqueous sodium chloride solution followed by drying over anhydrous sodium sulfate. Removal of methylene chloride by distillation gave the desired product, ethyl 5-[p-(bromoacetyl)phenoxy]-2,2-dimethylpentanoate, as an oily substance. ##STR12##

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux overnight
  3. customThe solvent was removed from the reaction mixture by distillation and, 500 ml of chloroform and 300 ml of a 5% aqueous hydrogen sodium carbonate solution
  4. additionwere added to the residue
  5. stirringAfter stirring the mixture
  6. washwashed successively with water
  7. dry with materialby drying over anhydrous sodium sulfate
  8. customRemoval of chloroform
  9. distillationby distillation
  10. customgave a residual oily substance
  11. washeluted

Sources & evidence

ORD record
ord-7553d2d9cac54c8081ccd19e462273a0
Source dataset
uspto-grants-1990_07
Patent number
US04942242

Reaction notes

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