Phenacyl bromide → 2-Propyl-3-(2-phenyl-2-oxoethoxy)phenol

HRID 342762Notes

Reaction equation

HRID 342762 reaction equation
[CH2:1]([C:4]1[C:10]([OH:11])=[CH:9][CH:8]=[CH:7][C:5]=1[OH:6])[CH2:2][CH3:3].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:19][C:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:21]>CN(C=O)C>[CH2:1]([C:4]1[C:10]([O:11][CH2:19][C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:21])=[CH:9][CH:8]=[CH:7][C:5]=1[OH:6])[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 6259Phenacyl bromideHCID 10796Cesium carbonateHCID 2620601,3-Benzenediol, propyl-

Product 1

HCID 543761242-Propyl-3-(2-phenyl-2-oxoethoxy)phenol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 2-propyl resorcinol (178.27 g; 1.171 mol) in dry DMF (1200 mL) was added cesium carbonate (104.95 g; 322.12 mmol). The mixture was stirred at room temperature and treated dropwise with a solution of 2-bromoacetophenone (58.29 G; 292.84 mmol) in dry DMF (500 mL) over 2 hours. The was stirred at ambient temperature for 64 hours. The reaction mixture was partitioned between isopropyl acetate and water. The aqueous was adjusted to pH 13 by addition of aq. 5N sodium hydroxide. The organic was dried over magnesium sulfate, filtered and evaporated to a residue. The residue was dissolved in methylene chloride (110 mL) and hexane (350 mL) and heated to reflux. The solution was cooled to -10° C. Stirring was continued for 1 hour. The title compound was recovered by filtration.

Workup

  1. stirringThe was stirred at ambient temperature for 64 hours
  2. customThe reaction mixture was partitioned between isopropyl acetate and water
  3. additionThe aqueous was adjusted to pH 13 by addition of aq. 5N sodium hydroxide
  4. dry with materialThe organic was dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated to a residue
  7. dissolutionThe residue was dissolved in methylene chloride (110 mL)
  8. temperaturehexane (350 mL) and heated to reflux
  9. temperatureThe solution was cooled to -10° C
  10. stirringStirring
  11. filtrationThe title compound was recovered by filtration

Sources & evidence

ORD record
ord-b59cb8e48faa4c4d85e0bc621804da61
Source dataset
uspto-grants-1999_01
Patent number
US05859051

Reaction notes

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