2-(2-Acetoxy-4-fluorophenoxy)ethanol → 2-(2-Hydroxy-4-fluorophenoxy)ethanol

HRID 1582756Notes

Reaction equation

HRID 1582756 reaction equation
C([O:4][C:5]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:6]=1[O:7][CH2:8][CH2:9][OH:10])(=O)C.[H-].[OH-].[Li+]>O1CCCC1.O>[OH:4][C:5]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:6]=1[O:7][CH2:8][CH2:9][OH:10]

Participants

5

Reactant 2

HCID 227183672-(2-Acetoxy-4-fluorophenoxy)ethanolHCID 86597229HCID 86597229, compound

Product 1

HCID 227182352-(2-Hydroxy-4-fluorophenoxy)ethanol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
90 °C

Procedure

2-(2-Acetoxy-4-fluorophenoxy)ethanol 1.53 g was dissolved in a mixed solvent of tetrahydrofuran 10 ml and water 5 ml, then lithium hydroxide monohydride 294 mg was added thereto, and the mixture was stirred at 90° C. After stirred for 10 hours, the reaction mixture was cooled and partitioned by adding water and ethyl acetate. The organic layer was washed with water and then with brine, dried over magnesium sulfate anhydride and evaporated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate system), whereby the title compound (1.07 g, 80%) was obtained as a colorless oil.

Workup

  1. stirringAfter stirred for 10 hours
  2. temperaturethe reaction mixture was cooled
  3. custompartitioned
  4. additionby adding water and ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialwith brine, dried over magnesium sulfate anhydride
  7. customevaporated
  8. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate system), whereby the title compound (1.07 g, 80%)
  9. customwas obtained as a colorless oil

Sources & evidence

ORD record
ord-12524f5734e5433b93ec789952030b17
Source dataset
uspto-grants-2004_05
Patent number
US06737425B1

Reaction notes

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