Water → HCID 54122965, compound

HRID 1390941Notes

Reaction equation

HRID 1390941 reaction equation
[OH:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([C:9]([CH3:25])([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:10][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:12])=[CH:4][CH:3]=1.[Br:26][CH2:27][CH2:28][CH2:29]Cl.O>CC(C)=O>[Br:26][CH2:27][CH2:28][CH2:29][O:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([C:9]([CH3:25])([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:10][C:11]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[O:12])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 80061-Bromo-3-chloropropaneHCID 54021829HCID 54021829, compound

Product 1

HCID 54122965HCID 54122965, compoundYield 85.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

Fifty grams (0.15 mol) of 4-hydroxy-3,5-dimethyl-β,β-diphenylpropiophenone (prepared as in Example 5), dissolved in 200 mls of acetone, are added, with stirring, to a reaction mixture consisting of 29 grams (0.184 mol) of 1-bromo-3-chloropropane in 300 mls of acetone and 42 grams (0.304 mol) of water-free potash. The preparation is boiled under reflux for one day and the precipitate is sucked off. The acetone is evaporated, the residue taken up with ether and a little acetone and, subsequently, washed with water. The ethereal phase is dried over sodium sulfate. The solvent is evaporated in vacuo. The residue is crystallized from acetone/petroleum ether. Fifty-two and five-tenths grams [85.5%] of 4-(3-bromopropoxy)-3,5-dimethyl-β,β-diphenylpropiophenone are obtained.

Workup

  1. additionare added
  2. temperatureunder reflux for one day
  3. customThe acetone is evaporated
  4. washa little acetone and, subsequently, washed with water
  5. dry with materialThe ethereal phase is dried over sodium sulfate
  6. customThe solvent is evaporated in vacuo
  7. customThe residue is crystallized from acetone/petroleum ether

Sources & evidence

ORD record
ord-b7be2de0cced49b99745cf94a87b348a
Source dataset
uspto-grants-1979_02
Patent number
US04140770

Reaction notes

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