Ethylene Glycol → HCID 178444386, compound

HRID 621397Notes

Reaction equation

HRID 621397 reaction equation
[OH-].[K+].C(O)CO.[CH2:7]([C@H:12]1[CH2:17][CH2:16][C@H:15]([C:18]2[N:23]=[CH:22][C:21]([O:24]C)=[CH:20][N:19]=2)[CH2:14][CH2:13]1)[CH2:8][CH2:9][CH2:10][CH3:11]>C(O)(=O)C>[CH2:7]([C@H:12]1[CH2:13][CH2:14][C@H:15]([C:18]2[N:23]=[CH:22][C:21]([OH:24])=[CH:20][N:19]=2)[CH2:16][CH2:17]1)[CH2:8][CH2:9][CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 14797Potassium HydroxideHCID 178444385HCID 178444385, compound

Product 1

HCID 178444386HCID 178444386, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

KOH (9.5 g, 0.17 mol) and ethylene glycol (100 ml) were added to 2-(trans-4-pentylcyclohexyl)-5-methoxypyrimidine (7.4 g, 0.028 mol) prepared in the same manner as in Example 1, followed by heating the mixture under reflux with stirring for 3 hours, cooling the resulting material, adding glacial acetic acid (30 ml) thereto, further adding water (100 ml), filtering the reaction mixture under suction through a filter, sufficiently washing the residue on the filter with water, three times recrystallizing the residue from ethanol and removing ethanol under reduced pressure to obtain 2-(trans-4-pentylcyclohexyl)-5-hydroxypyrimidine (4.9 g, 0.020 mol) having a melting point of 190.0°~191.1° C.

Workup

  1. customprepared in the same manner as in Example 1
  2. temperatureby heating the mixture
  3. temperatureunder reflux
  4. temperaturecooling the resulting material
  5. filtrationfurther adding water (100 ml), filtering the reaction mixture under suction through a filter
  6. washsufficiently washing the residue on the
  7. filtrationfilter with water, three times
  8. customrecrystallizing the residue from ethanol
  9. customremoving ethanol under reduced pressure

Sources & evidence

ORD record
ord-21e3ada4a00240a48028a7b81d56851e
Source dataset
uspto-grants-1989_04
Patent number
US04824596

Reaction notes

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