Potassium Hydroxide → HCID 59512553, compound

HRID 1158451Notes

Reaction equation

HRID 1158451 reaction equation
[OH-].[K+].COCCC[O:8][C:9](=[O:25])[C:10]1[CH:15]=[CH:14][C:13]([CH:16]([F:18])[F:17])=[C:12]([O:19][CH2:20][CH2:21][CH2:22][O:23][CH3:24])[CH:11]=1>CO>[F:17][CH:16]([F:18])[C:13]1[CH:14]=[CH:15][C:10]([C:9]([OH:25])=[O:8])=[CH:11][C:12]=1[O:19][CH2:20][CH2:21][CH2:22][O:23][CH3:24]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 68617380HCID 68617380, compound

Product 1

HCID 59512553HCID 59512553, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1N aqueous KOH (6.7 mL, 6.7 mmol) is slowly added to a solution of 4-difluoromethyl-3-(3-methoxy-propoxy)-benzoic acid 3-methoxy-propyl ester (1.48 g, 4.45 mmol) in MeOH (5 mL) and the reaction mixture is stirred at RT for 60 h. For workup the mixture is concentrated under reduced pressure, the residue is taken up in 2N HCl (until a pH=1 is obtained) and extracted with ethyl acetate. The combined organic extracts are washed with brine, dried (Na2SO4), filtered and the solvent is evaporated to give the title compound. MS (LC-MS): 259.1 [M−H]+; tR (HPLC, Macherey-Nagel Nucleosil C18 column, 10-100% CH3CN/H2O/5 min, 100% CH3CN/3 min, CH3CN and H2O containing 0.1% TFA, flow: 1.5 mL/min): 4.89 min.

Workup

  1. concentrationFor workup the mixture is concentrated under reduced pressure
  2. customis obtained) and
  3. extractionextracted with ethyl acetate
  4. washThe combined organic extracts are washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customthe solvent is evaporated

Sources & evidence

ORD record
ord-c286200b445c4b7bb539c7316ee92b01
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

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