Ethanol → 5-(Octyloxy)-2-(4-octylphenyl)pyrimidine

HRID 1164766Notes

Reaction equation

HRID 1164766 reaction equation
[OH:1][C:2]1[CH:3]=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:10][CH:9]=2)=[N:6][CH:7]=1.C(O)C.[CH2:25](I)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32].N12CCCC=C1CCCCN2>C1(C)C=CC=CC=1>[CH2:25]([O:1][C:2]1[CH:7]=[N:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:10][CH:9]=2)=[N:4][CH:3]=1)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]

Participants

6

Reactant 4

HCID 702EthanolHCID 123801-IodooctaneHCID 9834010Diazabicyclo[5.4.0]undec-7-eneHCID 115293165-Hydroxy-2-(4-octylphenyl)pyrimidine

Product 1

HCID 145333915-(Octyloxy)-2-(4-octylphenyl)pyrimidineYield 70%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 5-hydroxy-2-(4-octylphenyl)pyrimidine (5 g, 0.018 mol) were added ethanol (50 ml), octyl iodide (12.6 g, 0.053 mol) and diazabicyclo[5.4.0]undec-7-ene (0.053 mol), followed by refluxing the mixture for 4 hours, dissolving the reaction mixture in toluene, sufficiently washing the solution with 2N-NaOH aqueous solution, further washing it with water, distilling off toluene and recrystallizing the residue from methanol (75 ml) to obtain 5-octyloxy-2-(4-octylphenyl)pyrimidine (5 g). This product exhibited liquid crystalline properties and its phase transition points were as follows: ##STR19##

Workup

  1. temperatureby refluxing the mixture for 4 hours
  2. washsufficiently washing the solution with 2N-NaOH aqueous solution
  3. washfurther washing it with water
  4. distillationdistilling off toluene
  5. customrecrystallizing the residue from methanol (75 ml)

Sources & evidence

ORD record
ord-0a474cab7289496492172a707c2bc90c
Source dataset
uspto-grants-1990_03
Patent number
US04906400

Reaction notes

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