Sulfuric Acid → 1-(4-Chlorophenyl)-2-methoxyethanone

HRID 482608

Reaction equation

HRID 482608 reaction equation
[CH3:1][O:2][CH2:3][C:4]#N.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([Mg]Br)=[CH:9][CH:8]=1.S(=O)(=O)(O)[OH:16]>C(OCC)C.O>[CH3:1][O:2][CH2:3][C:4]([C:10]1[CH:11]=[CH:12][C:7]([Cl:6])=[CH:8][CH:9]=1)=[O:16]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 74442MethoxyacetonitrileHCID 178478191HCID 178478191, compound

Product 1

HCID 3184091-(4-Chlorophenyl)-2-methoxyethanone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

To 25 g (281 mmole) of methoxyacetonitrile in 100 ml of diethyl ether at reflux was added 250 ml (250 mmole) of 1.0M 4-chlorophenyl magnesium bromide in diethyl ether. After refluxing for 30 minutes the reaction mixture was hydrolyzed with a solution of 30 ml of concentrated sulfuric acid in 100 ml of water. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate, concentrated in vacuo, and dissolved in hexanes. The insolubles were filtered away and the resultant solution was concentrated and distilled yielding a clear liquid. bp 105°-115° C. at 1 torr. The oil solidified on standing.

Workup

  1. temperatureAfter refluxing for 30 minutes the reaction mixture
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. dissolutiondissolved in hexanes
  6. filtrationThe insolubles were filtered away
  7. concentrationthe resultant solution was concentrated
  8. distillationdistilled
  9. customyielding a clear liquid

Sources & evidence

ORD record
ord-4c08224f7a6046bfaf0d51877c48ca84
Source dataset
uspto-grants-1998_08
Patent number
US05798311

Linked notes

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