Sodium Hydroxide → 2-(3-(Propan-2-yloxy)phenyl)acetic acid

HRID 343681Notes

Reaction equation

HRID 343681 reaction equation
C([O:4][C:5](=[O:17])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH:14]([CH3:16])[CH3:15])[CH:8]=1)(C)C.[OH-].[Na+]>C(O)C.O>[CH:14]([O:13][C:9]1[CH:8]=[C:7]([CH2:6][C:5]([OH:17])=[O:4])[CH:12]=[CH:11][CH:10]=1)([CH3:16])[CH3:15]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54166898Isopropyl 2-(3-isopropoxyphenyl)acetate

Product 1

HCID 166389242-(3-(Propan-2-yloxy)phenyl)acetic acid

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

Combine 3-isopropoxy-phenyl-acetic acid isopropyl ester 10.2 g, 43.2 mmol) and sodium hydroxide (2.08 g, 51.8 mmol) in 1/1 ethanol/water (80 mL). Heat to reflux. After 18 hours, remove the ethanol by evaporation in vacuo and acidify to pH=1 using an aqueous solution with 1M hydrochloric acid solution. Extract the aqueous solution 3 times with ethyl acetate. Extract the combined organic layers with water and saturated sodium chloride solution. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to obtain 3-isopropoxy-phenyl-acetic acid.

Workup

  1. temperatureHeat to reflux
  2. customremove the ethanol
  3. customby evaporation in vacuo
  4. extractionExtract the aqueous solution 3 times with ethyl acetate
  5. extractionExtract the combined organic layers with water and saturated sodium chloride solution
  6. dry with materialDry the organic layer over MgSO4
  7. filtrationfilter
  8. customevaporate in vacuo

Sources & evidence

ORD record
ord-70dfd92320f74292bee62f28536705b2
Source dataset
uspto-grants-1999_01
Patent number
US05861416

Reaction notes

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