Water → 4-Cyanophenyl 4-[(prop-2-en-1-yl)oxy]benzoate

HRID 742522Notes

Reaction equation

HRID 742522 reaction equation
[CH2:1]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1)[CH:2]=[CH2:3].[C:14]([C:16]1[CH:21]=[CH:20][C:19](O)=[CH:18][CH:17]=1)#[N:15].O>C(Cl)(Cl)Cl>[CH2:1]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([O:11][C:19]2[CH:20]=[CH:21][C:16]([C:14]#[N:15])=[CH:17][CH:18]=2)=[O:10])=[CH:7][CH:6]=1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 962WaterHCID 130194-CyanophenolHCID 4606904-(Prop-2-en-1-yloxy)benzoic acid

Product 1

HCID 149851184-Cyanophenyl 4-[(prop-2-en-1-yl)oxy]benzoateYield 77.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

15.0 g of PPE, 4.00 g (22.4 mmol) of the compound (12) and 2.66 g (22.3 mmol) of p-cyanophenol were dissolved in ml of chloroform under an argon gas atmosphere and the whole was stirred at room temperature overnight. After addition of water to the reaction mixture, the whole was extracted with methylene chloride. After removal of the solvent by distillation, the residue was purified by silica gel column chromatography to obtain 4.80 g of p-cyanophenyl p-allyloxybenzoate (17) as a white solid (yield: 76.7%).

Workup

  1. extractionthe whole was extracted with methylene chloride
  2. customAfter removal of the solvent
  3. distillationby distillation
  4. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-619c789cc3b64082989a30e7db5218b9
Source dataset
uspto-grants-1996_09
Patent number
US05554706

Reaction notes

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