1-Octanol → Octyl 4'-hydroxy-4-biphenylcarboxylate

HRID 2372675Notes

Reaction equation

HRID 2372675 reaction equation
[CH2:1]([OH:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[OH:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:25]=[CH:24][C:20]([C:21](O)=[O:22])=[CH:19][CH:18]=2)=[CH:13][CH:12]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>O>[CH2:1]([O:9][C:21]([C:20]1[CH:19]=[CH:18][C:17]([C:14]2[CH:15]=[CH:16][C:11]([OH:10])=[CH:12][CH:13]=2)=[CH:25][CH:24]=1)=[O:22])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 4

HCID 9571-OctanolHCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 3015564'-Hydroxy-4-biphenylcarboxylic acid

Product 1

HCID 14692993Octyl 4'-hydroxy-4-biphenylcarboxylateYield 87.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Fifteen grams of n-octanol, 7.5 g of 4-(4'-hydroxyphenyl)benzoic acid and 7.0 g of p-toluene-sulfonic acid were dissolved with 100 ml of toluene in a three necked flask with a dehydration, apparatus, and the mixture was refluxed for 15 hours. Water was added to the mixture to separate a toluene layer. Ten grams of 4-(4'-octyloxycarbonylphenyl)phenol (AB) were obtained by removing the toluene layer under reduced pressure followed concentration. (s)-4-(1-chloro-2-methylpropylcarbonyloxy)benzoic acid dispersed in 20 ml of carbon tetrachloride was reacted with 5 ml of thionyl chloride by refluxing for 3 hours. After removing the solvent (s)-4-(1-chloro-2-methylpropylcarbonyloxy)benzoic chloride (AC) was obtained. 1.5 g of (AC) was dissolved with mixed solvent of 80 ml of carbon tetrachloride and 10 ml of pyridine, and then 1.7 g of (AB) was added to the mixed solution with cooling and the mixture was allowed to stand overnight to obtain crystals.

Workup

  1. temperaturethe mixture was refluxed for 15 hours
  2. customto separate a toluene layer

Sources & evidence

ORD record
ord-3738d345859b4867a0d30536a1963626
Source dataset
uspto-grants-1992_03
Patent number
US05100579

Reaction notes

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