Iodine → 2-(3-Methylphenyl)acetophenone

HRID 1679431Notes

Reaction equation

HRID 1679431 reaction equation
[C:1](#N)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Mg].II.[CH3:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH2:16]Br.CC[O:23]CC>O>[C:2]1([C:1]([CH2:12][C:13]2[CH:20]=[CH:19][CH:18]=[C:15]([CH3:16])[CH:14]=2)=[O:23])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 807IodineHCID 3283Diethyl Ether2×HCID 7505BenzonitrileHCID 12099m-Xylyl bromideHCID 5462224Magnesium

Product 1

HCID 131736142-(3-Methylphenyl)acetophenone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of benzonitrile (58.5 g) in anhydrous ether (150 ml) is added dropwise with stirring to Grignard reagent which is prepared from magnesium turnings (14.6 g), a small amount of iodine and m-methylbenzylbromide (100 g) in anhydrous ether (800 ml) at moisture-free atmosphere. The mixture is refluxed for 6 hours. The reaction mixture is decomposed by adding water thereto, and the ether layer is separated and distilled to remove the solvent. The residue is mixed with 10% hydrochloric acid and the mixture is refluxed for 1.5 hours. After cooling, the mixture is extracted with ether. The ether layer is dried over anhydrous sodium sulfate and the solvent is distilled off to give crude m-methylbenzyl phenyl ketone (82 g).

Workup

  1. temperatureThe mixture is refluxed for 6 hours
  2. customthe ether layer is separated
  3. distillationdistilled
  4. customto remove the solvent
  5. additionThe residue is mixed with 10% hydrochloric acid
  6. temperaturethe mixture is refluxed for 1.5 hours
  7. temperatureAfter cooling
  8. extractionthe mixture is extracted with ether
  9. dry with materialThe ether layer is dried over anhydrous sodium sulfate
  10. distillationthe solvent is distilled off

Sources & evidence

ORD record
ord-f088f7247eec463997aef09cbab947cb
Source dataset
uspto-grants-1978_03
Patent number
US04080453

Reaction notes

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