Water → 2-(3-(Propan-2-yloxy)phenyl)acetic acid

HRID 1854584Notes

Reaction equation

HRID 1854584 reaction equation
[CH:1]([O:4][C:5]1[CH:6]=[C:7]([CH2:11][C:12]([O:14]C(C)C)=[O:13])[CH:8]=[CH:9][CH:10]=1)([CH3:3])[CH3:2].O.[OH-].[Li+]>O1CCCC1>[CH:1]([O:4][C:5]1[CH:6]=[C:7]([CH2:11][C:12]([OH:14])=[O:13])[CH:8]=[CH:9][CH:10]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 54166898Isopropyl 2-(3-isopropoxyphenyl)acetate

Product 1

HCID 166389242-(3-(Propan-2-yloxy)phenyl)acetic acidYield 97.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
66 °C

Procedure

Dissolve isopropyl 2-(3-isopropoxyphenyl)acetate (4.2 g, 17.8 mmol) in tetrahydrofuran (35.6 mL). Add water (35.6 mL) and lithium hydroxide (6.05 g, 248.8 mmol). Heat the reaction mixture to 66° C. overnight. Concentrate under reduced pressure to remove the tetrahydrofuran. Dilute the reaction mixture with water and wash with diethyl ether. Acidify the water layer with 5N HCl to pH 1. Extract the water layer with diethyl ether. Wash the diethyl ether extract with water and brine, dry over sodium sulfate, filter and concentrate under reduced pressure to give the title compound (3.37 g, 17.35 mmol). MS (m/z): 195.0 (M+1), 212.0 (M+18).

Workup

  1. concentrationConcentrate under reduced pressure
  2. customto remove the tetrahydrofuran
  3. additionDilute the reaction mixture with water
  4. washwash with diethyl ether
  5. extractionExtract the water layer with diethyl ether
  6. washWash the diethyl ether
  7. extractionextract with water and brine
  8. dry with materialdry over sodium sulfate
  9. filtrationfilter
  10. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-c637c19c093d4f0eb5c91abf9c6d7829
Source dataset
uspto-grants-2015_02
Patent number
US08962654B2

Reaction notes

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