4-Fluorophenol → HCID 560198, compound

HRID 2100473Notes

Reaction equation

HRID 2100473 reaction equation
C([O-])C.[Na+].[F:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.Cl[CH2:14][CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18]>C(O)C>[CH2:20]([O:19][C:17](=[O:18])[CH2:16][CH2:15][CH2:14][O:12][C:9]1[CH:10]=[CH:11][C:6]([F:5])=[CH:7][CH:8]=1)[CH3:21]

Participants

5

Reactant 3

HCID 97324-FluorophenolHCID 18474Ethyl 4-chlorobutyrateHCID 2723922Sodium ethoxide

Product 1

HCID 560198HCID 560198, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Under cooling (0° C.), sodium ethanolate (2.18 g, 32 mmol) was added to a mixture of 4-fluorophenol ([371-41-5], 3.00 g, 27 mmol), ethyl 4-chlorobutyrate ([3153-36-4], 4.84 g, 32 mmol) and ethanol (15 ml), and the reaction mixture was then refluxed overnight. The solvent was evaporated, the residue was taken up in ethyl ester and was washed with water. After drying (Na2SO4), the solvent was evaporated, and 4-(4-fluoro-phenoxy)-butyric acid ethyl ester was isolated from the residue by column chromatography (silica gel, ethyl acetate/heptane). 1H NMR (d6-DMSO): 1.29 (t, 3H), 2.11 (tt, 2H), 2.51 (t, 2H), 3.96 (t, 2H), 4.13 (q, 2H), 6.79-6.85 (m, 2H), 6.92-6.99 (m, 2H).

Workup

  1. temperaturethe reaction mixture was then refluxed overnight
  2. customThe solvent was evaporated
  3. washwas washed with water
  4. dry with materialAfter drying (Na2SO4)
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-4c880e51c4b647fcab12a7b0553f07bc
Source dataset
uspto-grants-2009_08
Patent number
US07572801B2

Reaction notes

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