Hydrochloric Acid → 1-Propanone, 2,2-dimethyl-1-(4-phenoxyphenyl)-

HRID 436371

Reaction equation

HRID 436371 reaction equation
[Mg].II.[CH:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][C:14](Br)=[CH:13][CH:12]=2)=[CH:6][CH:5]=1.[CH3:18][C:19]([CH3:24])([CH3:23])[C:20](Cl)=[O:21].Cl>O1CCCC1>[O:10]([C:11]1[CH:16]=[CH:15][C:14]([C:20](=[O:21])[C:19]([CH3:24])([CH3:23])[CH3:18])=[CH:13][CH:12]=1)[C:7]1[CH:8]=[CH:9][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 807IodineHCID 75654-Bromodiphenyl EtherHCID 62493Pivaloyl chlorideHCID 5462224Magnesium

Product 1

HCID 416331-Propanone, 2,2-dimethyl-1-(4-phenoxyphenyl)-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a flask containing 33.6 g. of magnesium and a few crystals of iodine, is added 50 to 70 ml. of a solution of 300 g. of 4-bromodiphenyl ether in 500 ml. of absolute tetrahydrofuran. The remainder of the solution is added as needed to maintain a gentle reflux and the resulting mixture heated to reflux for 30 minutes. The resulting mixture is then added to a solution of trimethylacetyl chloride in 500 ml. of absolute tetrahydrofuran at a rate so as to maintain a temperature of from 40° to 50° C. The resulting mixture is then stirred at ambient temperture for 1 hour. 200 ml. of 2N. hydrochloric acid is then added. The organic layer is washed twice with one liter of 2N. sodium carbonate solution, dried and evaporated in vacuo to a liquid. The liquid thus obtained is distilled under reduced pressure to obtain p-phenoxypivalophenone, b.p. 136° -139° C. at 0.1 mm/Hg.

Workup

  1. additionTo a flask containing 33.6 g
  2. additionThe remainder of the solution is added
  3. temperatureto maintain
  4. temperaturea gentle reflux
  5. temperaturethe resulting mixture heated
  6. temperatureto reflux for 30 minutes
  7. washThe organic layer is washed twice with one liter of 2N
  8. dry with materialsodium carbonate solution, dried
  9. customevaporated in vacuo to a liquid
  10. customThe liquid thus obtained
  11. distillationis distilled under reduced pressure

Sources & evidence

ORD record
ord-214717a6e1884ed698d16f5629178edb
Source dataset
uspto-grants-1977_02
Patent number
US04008327

Linked notes

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