4'-Octyl-4-biphenylcarboxylic acid chloride → 4'-Octyl-4-biphenylcarboxylic acid p-(2-methylbutyloxycarbonyloxy)phenyl ester

HRID 1905600Notes

Reaction equation

HRID 1905600 reaction equation
[CH3:1][CH:2]([CH2:15][CH3:16])[CH2:3][O:4][C:5]([O:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)=[O:6].[CH2:17]([C:25]1[CH:30]=[CH:29][C:28]([C:31]2[CH:36]=[CH:35][C:34]([C:37](Cl)=[O:38])=[CH:33][CH:32]=2)=[CH:27][CH:26]=1)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>N1C=CC=CC=1.C1(C)C=CC=CC=1>[CH3:1][CH:2]([CH2:15][CH3:16])[CH2:3][O:4][C:5]([O:7][C:8]1[CH:9]=[CH:10][C:11]([O:14][C:37]([C:34]2[CH:33]=[CH:32][C:31]([C:28]3[CH:29]=[CH:30][C:25]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:26][CH:27]=3)=[CH:36][CH:35]=2)=[O:38])=[CH:12][CH:13]=1)=[O:6]

Participants

5

Reactant 2

HCID 147459674'-Octyl-4-biphenylcarboxylic acid chlorideHCID 20214693p-(2-Methylbutyloxycarbonyloxy)phenol

Product 1

HCID 137419824'-Octyl-4-biphenylcarboxylic acid p-(2-methylbutyloxycarbonyloxy)phenyl ester

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 1140TolueneSolvent2×

Conditions

Temperature
60 °C

Procedure

p-(2-Methylbutyloxycarbonyloxy)phenol (0.25 g) prepared in the above (i) was dissolved in pyridine (5 ml) and cooled with ice, followed by dropwise adding a solution of 4'-octyl-4-biphenylcarboxylic acid chloride (0.37 g) dissolved in toluene (5 ml), heating on a water bath at 60° C., reacting the mixture, adding toluene (50 ml), separating the toluene layer, washing with 6N-hydrochloric acid, further with 2N-NaOH aqueous solution, then with a saturated NaCl aqueous solution to make the layer neutral, drying over sodium sulfate, concentrating, and twice recrystallizing from a mixed solution of ethyl acetate (20 ml) and ethanol (10 ml) to obtain the objective 4'-octyl-4-biphenylcarboxylic acid p-(2-methylbutyloxycarbonyloxy)phenyl ester. This product exhibited SA phase and Ch phase and its phase transition points, C-SA point, SA-Ch point, and Ch-I point were 78.3° C., 150.2° C. and 165.2° C., respectively. Further its values of elemental analysis accorded well with its calculated values as follows:

Workup

  1. temperaturecooled with ice
  2. customseparating the toluene layer
  3. washwashing with 6N-hydrochloric acid, further with 2N-NaOH aqueous solution
  4. dry with materialdrying over sodium sulfate
  5. concentrationconcentrating
  6. customtwice recrystallizing from a mixed solution of ethyl acetate (20 ml) and ethanol (10 ml)

Sources & evidence

ORD record
ord-26fc1217fce84ad39de8582060e7e310
Source dataset
uspto-grants-1987_03
Patent number
US04647398

Reaction notes

Loading…