Potassium Hydroxide → HCID 18461284, compound

HRID 2303847Notes

Reaction equation

HRID 2303847 reaction equation
C([O:7][C:8]1[CH:13]=[C:12]([CH3:14])[C:11]([O:15][CH2:16][O:17][CH3:18])=[C:10]([CH3:19])[CH:9]=1)(=O)C(C)(C)C.[OH-].[K+]>CO>[CH3:18][O:17][CH2:16][O:15][C:11]1[C:12]([CH3:14])=[CH:13][C:8]([OH:7])=[CH:9][C:10]=1[CH3:19]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 18461391HCID 18461391, compound

Product 1

HCID 18461284HCID 18461284, compoundYield 100.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

8.09 g of crude 4-methoxymethoxy-3,5-dimethylphenyl pivaloate were dissolved in 30 ml of methanol. To the resulting solution, 30 ml of a solution of 3.40 g of potassium hydroxide in methanol were added dropwise, followed by stirring at room temperature for 4 hours. The reaction mixture was concentrated by evaporation. Water was added to the residue. The mixture was neutralized with 3N hydrochloric acid and sodium bicarbonate, followed by extraction with ethyl acetate. The extract was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by chromatography through a silica gel column (eluting solvent: n-hexane/ethyl acetate=4/1), whereby 5.58 g of the title compound were obtained.

Workup

  1. concentrationThe reaction mixture was concentrated by evaporation
  2. additionWater was added to the residue
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customThe residue was purified by chromatography through a silica gel column (eluting solvent: n-hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-c828932959ba4e44966a128154e26984
Source dataset
uspto-grants-2002_08
Patent number
US06432993B1

Reaction notes

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