Hydrochloric Acid → Ethyl acetate hexane

HRID 1678601Notes

Reaction equation

HRID 1678601 reaction equation
F[C:2]1[CH:3]=[C:4](C[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:5]=[CH:6][C:7]=1OCC1C(C)=CC(C)=CC=1C.[OH-].[Na+].Cl>C(O)C>[C:21]([O:23][CH2:24][CH3:25])(=[O:22])[CH3:20].[CH3:4][CH2:3][CH2:2][CH2:7][CH2:6][CH3:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 23136333HCID 23136333, compound

Product 1

HCID 21226206Ethyl acetate hexaneYield 99.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 3-fluoro-4-[(2,4,6-trimethylphenyl)methoxy]benzenepropanoate (363 mg, 1.1 mmol), a 2 N aqueous sodium hydroxide solution (1.5 mL) and ethanol (5 mL) was stirred at 60° C. for 1.5 hours. The reaction solution was ice-cooled and acidified with 1 N hydrochloric acid, and then the solvent was distilled off under reduced pressure. The residue was dissolved in methylene chloride, and the mixture was washed with water and saturated brine and dried over magnesium sulfate. Then, the solvent was distilled off under reduced pressure, and the resulting crystals were recrystallized from ethyl acetate/hexane (190 mg, yield 57%).

Workup

  1. temperaturecooled
  2. distillationthe solvent was distilled off under reduced pressure
  3. dissolutionThe residue was dissolved in methylene chloride
  4. washthe mixture was washed with water and saturated brine
  5. dry with materialdried over magnesium sulfate
  6. distillationThen, the solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-cc20106cb5f94bdaa9adb426655e0662
Source dataset
uspto-grants-2011_08
Patent number
US08008525B2

Reaction notes

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