Oxalic Acid → 2-(4,6-Dimethylpyrimidin-2-yl)oxy-3,3dimethylbutyric acid

HRID 1073026Notes

Reaction equation

HRID 1073026 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([O:9][CH:10]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:11]([O:13]C)=[O:12])[N:3]=1.[OH-].[K+].C1(C)C=CC=CC=1.C(O)(=O)C(O)=O>CO.O>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([O:9][CH:10]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:11]([OH:13])=[O:12])[N:3]=1

Participants

7

Reactant 4

HCID 971Oxalic AcidHCID 1140TolueneHCID 14797Potassium HydroxideHCID 15070275Methyl 2-(4,6-dimethylpyrimidin-2-yl)oxy3,3-dimethylbutyrate

Product 1

HCID 150702762-(4,6-Dimethylpyrimidin-2-yl)oxy-3,3dimethylbutyric acidYield 84.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

1.5 g of methyl 2-(4,6-dimethylpyrimidin-2-yl)oxy3,3-dimethylbutyrate was dissolved in 10 ml of methanol, and 10 ml of an aqueous solution containing 0.5 g of potassium hydroxide was added thereto. The mixture was stirred at room temperature for 12 hours and then shaked with 210 ml of toluene and 30 ml of water in a separatory funnel. The aqueous layer was acidified with an oxalic acid aqueous solution and extracted with 100 ml of ethyl ether. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain 1.2 g of the desired product.

Workup

  1. additionwas added
  2. extractionextracted with 100 ml of ethyl ether
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-01222139f9bc4c9bb3eb5df0f4a7f1da
Source dataset
uspto-grants-1990_11
Patent number
US04968340

Reaction notes

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