Diethylene Glycol → 5-Hydroxy-2-(4-octylphenyl)pyrimidine

HRID 1164765Notes

Reaction equation

HRID 1164765 reaction equation
C[O:2][C:3]1[CH:4]=[N:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:11][CH:10]=2)=[N:7][CH:8]=1.C(O)COCCO.[OH-].[Na+]>C(O)(=O)C>[OH:2][C:3]1[CH:8]=[N:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:11][CH:10]=2)=[N:5][CH:4]=1

Participants

5

Reactant 3

HCID 8117Diethylene GlycolHCID 14798Sodium HydroxideHCID 147447645-Methoxy-2-(4-octylphenyl)pyrimidine

Product 1

HCID 115293165-Hydroxy-2-(4-octylphenyl)pyrimidineYield 88.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
200 °C

Procedure

To 5-methoxy-2-(4-octylphenyl)pyrimidine (53.9 g, 0.18 mol) were added diethylene glycol (500 ml) and NaOH (43.4 g, 1.08 mol), followed by agitating the mixture at about 200° C. for 2 hours, pouring the resulting material in acetic acid (700 ml), collecting deposited crystals and recrystallizing the crystals from a mixed solvent of heptane (100 ml) with ethyl acetate (10 ml) to obtain 5-hydroxy-2-(4-octylphenyl)pyrimidine (45.2 g) (m.p.: 147.3-148.7 ° C.).

Workup

  1. customcollecting
  2. customrecrystallizing the crystals from a mixed solvent of heptane (100 ml) with ethyl acetate (10 ml)

Sources & evidence

ORD record
ord-93b66cc3e29a4bd39d746ef22a6d2405
Source dataset
uspto-grants-1990_03
Patent number
US04906400

Reaction notes

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