Potassium Hydroxide → HCID 18647438, compound

HRID 345719Notes

Reaction equation

HRID 345719 reaction equation
[OH:1][C:2]1[CH:3]=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][CH3:22])=[CH:16][CH:15]=3)=[CH:10][CH:9]=2)=[N:6][CH:7]=1.[OH-].[K+].[CH3:25][C@@H:26]([CH2:33][CH3:34])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]Br>C(O)C>[CH3:25][C@@H:26]([CH2:33][CH3:34])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][O:1][C:2]1[CH:7]=[N:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([C:14]3[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][CH3:22])=[CH:16][CH:15]=3)=[CH:12][CH:13]=2)=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 13548107(6S)-1-Bromo-6-methyloctaneHCID 199911075-Hydroxy-2(4'-propyl-biphenyl-4-yl)pyrimidine

Product 1

HCID 18647438HCID 18647438, compoundYield 62.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-Hydroxy-2(4'-propyl-biphenyl-4-yl)pyrimidine (10 g, 0.034 mol) was dissolved in ethanol (100 ml), followed by adding KOH (2.1 g, 0.037 mol), refluxing the mixture, dropwise adding (S)-6-methyloctyl bromide (7.7 g, 0.037 mol) over about 15 minutes, further refluxing the mixture for 5 hours, distilling off ethanol (80 ml), dissolving the residue in toluene (100 ml), transferring the solution into a separating funnel, sufficiently washing it with a 2N-NaOH aqueous solution, washing it with water until the washing water became neutral, drying the resulting organic layer over anhydrous magnesium sulfate, distilling off toluene and recrystallizing the residue from ethanol (200 ml) to obtain (S)-5-(6'-methyloctyloxy)-2(4'-propylbiphenyl-4-yl)pyrimidine (8.9 g). This product was a liquid crystal and exhibited the following phase transition points (also see Table 1): ##STR86##

Workup

  1. temperaturefurther refluxing the mixture for 5 hours
  2. distillationdistilling off ethanol (80 ml)
  3. dissolutiondissolving the residue in toluene (100 ml)
  4. washsufficiently washing it with a 2N-NaOH aqueous solution
  5. washwashing it with water until the washing water
  6. dry with materialdrying the resulting organic layer over anhydrous magnesium sulfate
  7. distillationdistilling off toluene
  8. customrecrystallizing the residue from ethanol (200 ml)

Sources & evidence

ORD record
ord-6ff6fa5f50eb4353bc5a660acb299f6b
Source dataset
uspto-grants-1991_10
Patent number
US05059340

Reaction notes

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