Lithium Hydroxide → HCID 23436260, compound

HRID 2121180Notes

Reaction equation

HRID 2121180 reaction equation
C[O:2][C:3](=[O:25])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)=[CH:6][C:5]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH3:24].[Li+].[OH-]>CO>[N:14]1[CH:15]=[CH:16][CH:17]=[C:12]([O:11][CH2:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:25])=[O:2])=[C:5]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[CH3:24])[CH:6]=2)[CH:13]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 10759063HCID 10759063, compound

Product 1

HCID 23436260HCID 23436260, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The 4-(3-pyridyloxymethyl)-2-(2-methylphenyl)benzoic acid methyl ester prepared in Example 204D (160 mg, 0.48 mmol) was dissolved in 5 mL of methanol and 1 mL of saturated aqueous LiOH was added. The reaction was heated to reflux for 1 hour. The reaction was then evaporated and 1 mL of formic acid was added to acidify the crude product 1 to pH=3. The reaction was evaporated again to remove formic acid and 5 mL of ethyl acetate and 1 mL of H2O were added to completely solubilize the reaction mixture. The aqueous layer was extracted with ethyl acetate (3×5 mL) and all the ethyl acetate layers were combined and dried over Na2SO4, filtered and evaporated to give 4-(3-pyridyloxymethyl)-2-(2-methylphenyl)benzoic acid (131 mg, 86%) as an oil.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 1 hour
  3. customThe reaction was then evaporated
  4. addition1 mL of formic acid was added
  5. customThe reaction was evaporated again
  6. customto remove formic acid and 5 mL of ethyl acetate and 1 mL of H2O
  7. additionwere added
  8. extractionThe aqueous layer was extracted with ethyl acetate (3×5 mL) and all the ethyl acetate layers
  9. dry with materialdried over Na2SO4
  10. filtrationfiltered
  11. customevaporated

Sources & evidence

ORD record
ord-fd3e8846f12f4e088db6029888f3b8e7
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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