Hydrochloric Acid → [4-(4-Phenylbutoxy)phenoxy]acetic acid

HRID 2422212Notes

Reaction equation

HRID 2422212 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:24]=[CH:23][C:15]([O:16][CH2:17][C:18]([O:20]CC)=[O:19])=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[OH-].[Li+].O1CCCC1.Cl>O.CO>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:13]=[CH:14][C:15]([O:16][CH2:17][C:18]([OH:20])=[O:19])=[CH:23][CH:24]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 85970854Ethyl [4-(4-phenylbutoxy)phenoxy]acetate

Product 1

HCID 23083004[4-(4-Phenylbutoxy)phenoxy]acetic acidYield 89%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of ethyl [4-(4-phenylbutoxy)phenoxy]acetate (0.59 g, 1.8 mmol), lithium hydroxide monohydrate (0.15 g, 3.6 mmol), tetrahydrofuran (5 mL), methanol (1 mL) and water (3 mL) was stirred at room temperature for 48 hrs. The mixture was acidified with 1N hydrochloric acid, and extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was recrystallized from ethyl acetate to give the title compound (0.48 g, yield 89%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-889b064c97b649cbbf2363144e3c7358
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Reaction notes

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