Acetic Acid → 2-(4-(Octyloxy)phenyl)pyrimidin-5-ol

HRID 330221Notes

Reaction equation

HRID 330221 reaction equation
[OH-].[Na+].C([O:5][C:6]1[CH:7]=[N:8][C:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:14][CH:13]=2)=[N:10][CH:11]=1)C.O.C(O)(=O)C>C(O)COCCO>[OH:5][C:6]1[CH:7]=[N:8][C:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:14][CH:13]=2)=[N:10][CH:11]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 144963945-Ethoxy-2-(4-octyloxyphenyl)pyrimidine

Product 1

HCID 144963952-(4-(Octyloxy)phenyl)pyrimidin-5-olYield 66.1%

Reagents, catalysts & solvents 1

HCID 8117Diethylene GlycolSolvent

Procedure

NaOH (58.4 g) was added to a solution of 5-ethoxy-2-(4-octyloxyphenyl)pyrimidine (48 g) dissolved in diethylene glycol (300 ml), followed by keeping the mixture at 220° C. for 3 hours, allowing the resulting material to cool down, adding water and acetic acid, filtering off deposited crystals, and recrystallizing from ethanol to obtain 5-hydroxy-2-(4-octyloxyphenyl)pyrimidine (29 g, m.p.: 131.2°-132.5° C.)

Workup

  1. customat 220° C.
  2. customfor 3 hours
  3. temperatureto cool down
  4. filtrationfiltering off
  5. customrecrystallizing from ethanol

Sources & evidence

ORD record
ord-a498bef9631944c9bdfc288c20672c99
Source dataset
uspto-grants-1990_01
Patent number
US04895671

Reaction notes

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