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

HRID 727900Notes

Reaction equation

HRID 727900 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-9e95dc354f314037a65137aacf18ed72
Source dataset
uspto-grants-1991_09
Patent number
US05045552

Reaction notes

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