1-Bromooctane → 5-Ethoxy-2-(4-octyloxyphenyl)pyrimidine

HRID 330220Notes

Reaction equation

HRID 330220 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[N:6][C:7]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)=[N:8][CH:9]=1)[CH3:2].[OH-].[K+].[CH2:19](Br)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]>C(O)C>[CH2:1]([O:3][C:4]1[CH:9]=[N:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:12][CH:11]=2)=[N:6][CH:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 81401-BromooctaneHCID 14797Potassium HydroxideHCID 1358116944-(5-Ethoxypyrimidin-2-yl)phenol

Product 1

HCID 144963945-Ethoxy-2-(4-octyloxyphenyl)pyrimidineYield 77.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5-ethoxy-2-(4-hydroxyphenyl)pyrimidine (40 g) dissolved in ethanol (340 ml) were added potassium hydroxide (11.2 g) and octyl bromide (35.8 g), followed by keeping the mixture under reflux for 3 hours, distilling off ethanol (about 300 ml), extracting the residue with toluene (500 ml), washing the resulting organic layer with 2N--NaOH aqueous solution, further washing with water until the washing water became neutral, distilling off low boiling substances in the organic layer and recrystallizing the residue from ethanol to obtain 5-ethoxy-2-(4-octyloxyphenyl)pyrimidine (46.9 g). This product exhibited a phase transition of ##STR11##

Workup

  1. temperatureunder reflux for 3 hours
  2. distillationdistilling off ethanol (about 300 ml)
  3. extractionextracting the residue with toluene (500 ml)
  4. washwashing the resulting organic layer with 2N
  5. washNaOH aqueous solution, further washing with water until the washing water
  6. distillationdistilling off low boiling substances in the organic layer
  7. customrecrystallizing the residue from ethanol

Sources & evidence

ORD record
ord-d205f5953700432aa0beba22110c4900
Source dataset
uspto-grants-1990_01
Patent number
US04895671

Reaction notes

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