Lithium hydroxide, monohydrate → 4-([1,1′-Biphenyl]-3-yloxy)butanoic acid

HRID 1377904Notes

Reaction equation

HRID 1377904 reaction equation
C([O:3][C:4](=[O:21])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:10]=1)C.O.[OH-].[Li+]>O1CCOCC1.O>[C:15]1([C:11]2[CH:10]=[C:9]([CH:14]=[CH:13][CH:12]=2)[O:8][CH2:7][CH2:6][CH2:5][C:4]([OH:21])=[O:3])[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 54546501HCID 54546501, compound

Product 1

HCID 104675934-([1,1′-Biphenyl]-3-yloxy)butanoic acidYield 103.1%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

To a solution in 2:1 dioxane/water (36 mL) of 4-(3-phenylphenoxy)butanoic acid ethyl ester (3.42 g, 12 mmol), prepared as in step 1, was added lithium hydroxide hydrate (1.42 g, 33.8 mmol) and the reaction mixture was stirred overnight at ambient temperature. The reaction mixture was concentrated in vacuo and the resulting solid was mostly dissolved in aqueous Na2CO3. The aqueous solution was decanted from a small amount of residual solid and extracted with ethyl ether. The ether extract was discarded and the aqueous phase was taken to pH 2 with HCl and extracted with ethyl acetate. The ethyl acetate extract was dried over MgSO4, filtered, and concentrated in vacuo to give 4-(3-phenylphenoxy)butanoic acid (3.17 g).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe resulting solid was mostly dissolved in aqueous Na2CO3
  3. customThe aqueous solution was decanted from a small amount of residual solid
  4. extractionextracted with ethyl ether
  5. extractionThe ether extract
  6. extractionextracted with ethyl acetate
  7. extractionThe ethyl acetate extract
  8. dry with materialwas dried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c6ada816f40f4847bb32b606537d8f4b
Source dataset
uspto-grants-1997_09
Patent number
US05665777

Reaction notes

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