Sodium Hydroxide → 4-(3-Methoxypropoxy)-3-methyl-2-pyridinemethanol

HRID 357556Notes

Reaction equation

HRID 357556 reaction equation
[OH-].[Na+].C([O:6][CH2:7][C:8]1[C:13]([CH3:14])=[C:12]([O:15][CH2:16][CH2:17][CH2:18][O:19][CH3:20])[CH:11]=[CH:10][N:9]=1)(=O)C>C(O)C>[OH:6][CH2:7][C:8]1[C:13]([CH3:14])=[C:12]([O:15][CH2:16][CH2:17][CH2:18][O:19][CH3:20])[CH:11]=[CH:10][N:9]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19600546(4-(3-Methoxypropoxy)-3-methylpyridin-2-yl)methyl acetate

Product 1

HCID 104657494-(3-Methoxypropoxy)-3-methyl-2-pyridinemethanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

500 mg of sodium hydroxide and 15 cc of ethanol were added to the 2-acetoxymethyl-4-(3-methoxypropoxy)-3-methylpyridine prepared above. The obtained mixture was stirred at 50° C. for one hour. After the completion of the reaction, the reaction mixture was distilled to remove the ethanol, followed by the addition of water. The obtained mixture was extracted with chloroform. The obtained chloroform layer was concentrated to obtain 450 mg of 2-hydroxymethyl-4-(3-methoxypropoxy)-3-methylpyridine as a brown oil.

Workup

  1. customprepared above
  2. customAfter the completion of the reaction
  3. distillationthe reaction mixture was distilled
  4. customto remove the ethanol
  5. additionfollowed by the addition of water
  6. extractionThe obtained mixture was extracted with chloroform
  7. concentrationThe obtained chloroform layer was concentrated

Sources & evidence

ORD record
ord-0c5e0365f68943ca898f63c1ec616065
Source dataset
uspto-grants-1998_11
Patent number
US05840910

Reaction notes

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