Sulfuric Acid → 1-(4-Chlorophenyl)-2,2-dimethylpropan-1-one

HRID 1638488Notes

Reaction equation

HRID 1638488 reaction equation
[CH3:1][C:2]([CH3:6])([CH3:5])[C:3]#N.[Cl:7][C:8]1[CH:13]=[CH:12][C:11](I)=[CH:10][CH:9]=1.[Mg].[OH:16]S(O)(=O)=O>O1CCCC1.[Na].O>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:3]([C:2]([CH3:6])([CH3:5])[CH3:1])=[O:16])=[CH:10][CH:9]=1

Participants

8

Reactant 4

HCID 1118Sulfuric AcidHCID 12416PivalonitrileHCID 125101-Chloro-4-iodobenzeneHCID 5462224Magnesium

Product 1

HCID 111380501-(4-Chlorophenyl)-2,2-dimethylpropan-1-oneYield 40%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 5360545SodiumSolvent

Procedure

Trimethyl acetonitrile (0.1 mol) in dry tetrahydrofuran (50 ml) was added dropwise with stirring to the Grignard reagent prepared form 4-chloro-iodobenzene (0.11 mol) and magnesium turnings (0.11 g atoms) in sodium dry ether (50 ml) at such a rate as to retain gentle reflux. The solution was refluxed for 4 hours, cooled to room temperature, and water (40 ml) added carefully. 2N H2SO4 (50 ml) was added and the ether solution washed with water (3×100 ml) and dried over anhydrous magnesium sulphate. Removal of the solvent gave a yellow oil which was distilled at the water pump to give tertiary butyl 4-chlorophenyl ketone (40%) as a colourless liquid b.p. 116°-128°/15 mm Hg.

Workup

  1. temperatureThe solution was refluxed for 4 hours
  2. washthe ether solution washed with water (3×100 ml)
  3. dry with materialdried over anhydrous magnesium sulphate
  4. customRemoval of the solvent
  5. customgave a yellow oil which
  6. distillationwas distilled at the water pump

Sources & evidence

ORD record
ord-021ec7b9ca0f4aa58093d9adc0ce798c
Source dataset
uspto-grants-1989_11
Patent number
US04880457

Reaction notes

Loading…