Sodium Hydroxide → 2-((4,6-Dimethylpyrimidin-2-yl)oxy)acetic acid

HRID 847118Notes

Reaction equation

HRID 847118 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([O:9][CH2:10][C:11]([O:13]CC)=[O:12])[N:3]=1.[OH-].[Na+]>C(O)C>[CH3:8][C:6]1[CH:7]=[C:2]([CH3:1])[N:3]=[C:4]([O:9][CH2:10][C:11]([OH:13])=[O:12])[N:5]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 3410252Ethyl 2-(4,6-dimethylpyrimidin-2-yl)oxyacetate

Product 1

HCID 198818052-((4,6-Dimethylpyrimidin-2-yl)oxy)acetic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2g (9.5mmol) of the ethyl ester prepared in Example 7 were dissolved in 20ml of ethanol. 25ml of an aqueous solution (10% by vol) of sodium hydroxide were then added to the solution. The reaction mixture was refluxed for 4 hours. After the reaction was complete, as confirmed by thin layer chromatography, the ethanol was evaporated off, the aqueous residue cooled, acidified to a pH of 2 and the product extracted into chloroform. Following drying first over anhydrous sodium sulphate and then by evaporation, 0.6g (yield 35% by weight) of a reddish oil were obtained which oil crystallised on standing.

Workup

  1. temperatureThe reaction mixture was refluxed for 4 hours
  2. customthe ethanol was evaporated off
  3. temperaturethe aqueous residue cooled
  4. extractionthe product extracted into chloroform
  5. dry with materialFollowing drying first over anhydrous sodium sulphate
  6. customby evaporation

Sources & evidence

ORD record
ord-c66387b1542d44ae88d0c2fcdcc585d9
Source dataset
uspto-grants-1992_08
Patent number
US05139563

Reaction notes

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