Pyridine → 3-Bromo-4-(2'-methylbutyl)benzoic acid 4'-octyloxy-4-biphenylyl ester

HRID 2072608Notes

Reaction equation

HRID 2072608 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH2:11][CH:12]([CH3:15])[CH2:13][CH3:14])[C:5](Cl)=[O:6].[OH:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])=[CH:25][CH:24]=2)=[CH:19][CH:18]=1.N1C=CC=CC=1>C1(C)C=CC=CC=1>[CH2:30]([O:29][C:26]1[CH:27]=[CH:28][C:23]([C:20]2[CH:19]=[CH:18][C:17]([O:16][C:5](=[O:6])[C:4]3[CH:8]=[CH:9][C:10]([CH2:11][CH:12]([CH3:15])[CH2:13][CH3:14])=[C:2]([Br:1])[CH:3]=3)=[CH:22][CH:21]=2)=[CH:24][CH:25]=1)[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]

Participants

5

Reactant 3

HCID 1049PyridineHCID 104943294-Hydroxy-4'-octyloxybiphenylHCID 538429803-Bromo-4-(2'-methylbutyl)benzoic acid chloride

Product 1

HCID 542993093-Bromo-4-(2'-methylbutyl)benzoic acid 4'-octyloxy-4-biphenylyl ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

This 3-bromo-4-(2'-methylbutyl)benzoic acid chloride (11.5 g, 0.04 mol) was dropwise added to a mixture of 4-hydroxy-4'-octyloxybiphenyl with anhydrous pyridine under ice cooling, followed by agitating the resulting mixture at 50°-60° C. for 2 hours, adding toluene (100 ml), sufficiently agitating the mixture, washing it with 6N-HCl, then with 2N-NaOH aqueous solution and further with water, further drying over anhydrous MgSO4, distilling off toluene and recrystallizing the residue from a mixture of ethanol (100 ml) with ethyl acetate (60 ml) to obtain 3-bromo-4-(2'-methylbutyl)benzoic acid 4'-octyloxy-4-biphenylyl ester (12.2 g), which exhibited liquid crystalline properties and had the following phase transistion points: ##STR45##

Workup

  1. stirringsufficiently agitating the mixture
  2. washwashing it with 6N-HCl
  3. dry with materialwith 2N-NaOH aqueous solution and further with water, further drying over anhydrous MgSO4
  4. distillationdistilling off toluene
  5. customrecrystallizing the residue
  6. additionfrom a mixture of ethanol (100 ml) with ethyl acetate (60 ml)

Sources & evidence

ORD record
ord-ac75e6b686804be3be2e8142ef414ebd
Source dataset
uspto-grants-1990_04
Patent number
US04913838

Reaction notes

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