Water → 4'-Octyloxybiphenyl p-allyloxybenzoate

HRID 742523Notes

Reaction equation

HRID 742523 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].[CH2:14]([O:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH:34]=[CH:33][C:32](O)=[CH:31][CH:30]=2)=[CH:25][CH:24]=1)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].O>C(Cl)(Cl)Cl>[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].[CH2:14]([O:22][C:23]1[CH:24]=[CH:25][C:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:27][CH:28]=1)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 962WaterHCID 4606904-(Prop-2-en-1-yloxy)benzoic acidHCID 104943294-Hydroxy-4'-octyloxybiphenyl

Product 1

HCID 867498084'-Octyloxybiphenyl p-allyloxybenzoateYield 86.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

15.0 g of PPE, 2.65 g (15.2 mmol) of the compound (12) and 4.50 g (13.4 mmol) of 4-octyloxy-4'-hydroxybiphenyl were dissolved in 120 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 5.30 g of 4- (4'-octyloxybiphenyl p-allyloxybenzoate (25) as a white solid (yield: 86.2%).

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-8784e778b3304a33a343d1f6f676858a
Source dataset
uspto-grants-1996_09
Patent number
US05554706

Reaction notes

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