Methyl Ethyl Ketone → 4-(4-Prop-2-enoxyphenyl)benzonitrile

HRID 1982747Notes

Reaction equation

HRID 1982747 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)#[N:2].[CH2:16](Br)[CH:17]=[CH2:18].C(=O)([O-])[O-].[K+].[K+].CC(=O)CC>O>[CH2:18]([O:15][C:12]1[CH:13]=[CH:14][C:9]([C:6]2[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=2)=[CH:10][CH:11]=1)[CH:17]=[CH2:16]

Participants

6

Reactant 4

HCID 6569Methyl Ethyl KetoneHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 1406104'-Hydroxy-4-biphenylcarbonitrile

Product 1

HCID 23419874-(4-Prop-2-enoxyphenyl)benzonitrileYield 91.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution prepared by adding 20 g of 4-cyano-4′-hydroxybiphenyl, 20 g of allyl bromide and 25 g of potassium carbonate to 250 ml of 2-butanone was refluxed for 7 hours. Water was added to the reaction solution for liquid-liquid separation, and the organic layer was washed with water and dried with anhydrous magnesium sulfate. The solvent was evaporated away, and the resulting residue was purified through silica gel column chromatography using toluene as an eluent solvent and then further recrystallized from ethanol to obtain 22 g of 4-allyloxy-4′-cyanobiphenyl.

Workup

  1. customA solution prepared
  2. temperaturewas refluxed for 7 hours
  3. washthe organic layer was washed with water
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customThe solvent was evaporated away
  6. customthe resulting residue was purified through silica gel column chromatography
  7. customfurther recrystallized from ethanol

Sources & evidence

ORD record
ord-d7eac201409d43deb09cba2b530eecf4
Source dataset
uspto-grants-2009_06
Patent number
US07541071B2

Reaction notes

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