Lithium hydroxide, monohydrate → HCID 15675487, compound

HRID 1377902Notes

Reaction equation

HRID 1377902 reaction equation
O1CCOCC1.O.C([O:10][C:11](=[O:28])[CH2:12][CH2:13][CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:18][CH:17]=1)C.O.[OH-].[Li+]>O1CCOCC1>[C:22]1([C:19]2[CH:20]=[CH:21][C:16]([O:15][CH2:14][CH2:13][CH2:12][C:11]([OH:28])=[O:10])=[CH:17][CH:18]=2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 168937Lithium hydroxide, monohydrate2×HCID 218864351,4-Dioxane--water (1/1)HCID 54135941Ethyl 4-[([1,1'-biphenyl]-4-yl)oxy]butanoate

Product 1

HCID 15675487HCID 15675487, compoundYield 67.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A suspension in 1:1 dioxane/water (70 mL) of 4-(4-phenylphenoxy)butanoic acid ethyl ester (10.29 g, 36 mmol), prepared as in step 1, and lithium hydroxide hydrate (2.05 g, 49 mmol) was heated at reflux for 18 hours. Dioxane (35 mL) was then added and an additional 2.0 equivalents of lithium hydroxide hydrate was added four hours later. The reaction mixture was heated at reflux for two more hours, then was cooled to ambient temperature and concentrated in vacuo. The resulting white solids were shaken with ethyl ether and aqueous 1M NaOH and the residual solid (4-(4-phenylphenoxy)butyric acid, 3.53 g) was filtered off. The organic phase was discarded and the aqueous phase was acidified with concentrated HCl. The aqueous phase was extracted with ethyl acetate. The ethyl acetate extracts were dried over MgSO4, filtered, and concentrated in vacuo to give an additional 6.25 g of 4-(4-phenylphenoxy)butanoic acid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 hours
  3. temperatureThe reaction mixture was heated
  4. temperatureat reflux for two more hours
  5. concentrationconcentrated in vacuo
  6. filtrationthe residual solid (4-(4-phenylphenoxy)butyric acid, 3.53 g) was filtered off
  7. extractionThe aqueous phase was extracted with ethyl acetate
  8. dry with materialThe ethyl acetate extracts were dried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9672af3967344190976d8e7893b23318
Source dataset
uspto-grants-1997_09
Patent number
US05665777

Reaction notes

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