p-Octylbenzoic acid → p-n-Octylbenzoic acid 4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester

HRID 482815Notes

Reaction equation

HRID 482815 reaction equation
C(C1C=CC(C(Cl)=O)=CC=1)CCCCCCC.[CH2:18]([C:26]1[CH:34]=[CH:33][C:29]([C:30]([OH:32])=[O:31])=[CH:28][CH:27]=1)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].S(Cl)(Cl)=O.[CH3:39][CH:40]([CH2:58][CH3:59])[CH2:41][O:42][C:43]([C:45]1[CH:50]=[CH:49][C:48]([C:51]2[CH:56]=[CH:55][C:54](O)=[CH:53][CH:52]=2)=[CH:47][CH:46]=1)=[O:44]>C1(C)C=CC=CC=1.N1C=CC=CC=1>[CH3:39][CH:40]([CH2:58][CH3:59])[CH2:41][O:42][C:43]([C:45]1[CH:50]=[CH:49][C:48]([C:51]2[CH:56]=[CH:55][C:54]([O:31][C:30](=[O:32])[C:29]3[CH:28]=[CH:27][C:26]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:34][CH:33]=3)=[CH:53][CH:52]=2)=[CH:47][CH:46]=1)=[O:44]

Participants

7

Reactant 4

HCID 19147p-Octylbenzoic acidHCID 24386Thionyl ChlorideHCID 170865Benzoyl chloride, 4-octyl-HCID 139075372-Methylbutyl 4'-hydroxybiphenyl-4-carboxylate

Product 1

HCID 13530953p-n-Octylbenzoic acid 4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 1140TolueneSolvent

Procedure

p-n-Octylbenzoic acid chloride prepared from 7 g of p-n-octylbenzoic acid and excess thionyl chloride was dissolved in toluene, and the solution was admixed with a pyridine solution of 8.3 g of said 4-hydroxy-4'-biphenylcarboxylic acid 2-methylbutyl ester for reaction at 80° C. for 3 hours. The crude product was obtained in the same manner as described in Example 1 and recrystallized twice from ethyl acetate to obtain p-n-octylbenzoic acid 4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester.

Workup

  1. customThe crude product was obtained in the same manner
  2. customrecrystallized twice from ethyl acetate

Sources & evidence

ORD record
ord-9936b72136db40618d3c169a9437e706
Source dataset
uspto-grants-1986_03
Patent number
US04576732

Reaction notes

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