Sodium Hydroxide → 5-Acetyl-2-isopropoxy-benzoic acid

HRID 2251271

Reaction equation

HRID 2251271 reaction equation
C[O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([C:10](=[O:12])[CH3:11])[CH:7]=[CH:6][C:5]=1[O:13][CH:14]([CH3:16])[CH3:15].[OH-].[Na+]>C1COCC1>[C:10]([C:8]1[CH:7]=[CH:6][C:5]([O:13][CH:14]([CH3:16])[CH3:15])=[C:4]([CH:9]=1)[C:3]([OH:17])=[O:2])(=[O:12])[CH3:11]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 690374735-Acetyl-2-isopropoxy-benzoic acid methyl ester

Product 1

HCID 690386975-Acetyl-2-isopropoxy-benzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To 25.8 mmol 5-acetyl-2-isopropoxy-benzoic acid methyl ester in 100 ml THF was 400 mmol 2 M aq NaOH, and the mixture was heated at 80° C. for 2 h. The mixture en cooled to RT and extracted twice with ether. The aqueous phase was acidified with q hydrochloric acid and extracted 3 times with ethyl acetate. The combined organic were dried with Na2SO4. Evaporation in vacuo followed by trituration in ether ed the title compound. MS (m/e): 221.2 ([M−H]−, 100%)

Workup

  1. temperatureThe mixture en cooled to RT
  2. extractionextracted twice with ether
  3. extractionextracted 3 times with ethyl acetate
  4. dry with materialThe combined organic were dried with Na2SO4
  5. customEvaporation in vacuo

Sources & evidence

ORD record
ord-1aa2ad9e0bfd4ca3bc4eafd4039a218b
Source dataset
uspto-grants-2008_01
Patent number
US07319099B2

Linked notes

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