Water → HCID 21187882, compound

HRID 1383520Notes

Reaction equation

HRID 1383520 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:14]=[CH:15][C:16]=2[O:17][CH:18]([F:20])[F:19])[C:10]([O:12]C)=[O:11])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].O>CO>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:14]=[CH:15][C:16]=2[O:17][CH:18]([F:19])[F:20])[C:10]([OH:12])=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 21187956HCID 21187956, compound

Product 1

HCID 21187882HCID 21187882, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 3-cyclopentyloxy-4-difluoromethoxybenzoate (0.6 g; that is prepared as described in Reference Example 41) in methanol (10 mL) is treated with potassium carbonate (0.35 g) and water (4 mL), and then it is heated at reflux for 3 hours. Methanol is evaporated off under reduced pressure, and the residue is dissolved in water (40 mL). The solution is washed with diethyl ether (40 mL), acidified with concentrated hydrochloric acid, and extracted with ethyl acetate (3×40 mL). The combined ethyl acetate extracts are dried over magnesium sulfate and evaporated under reduced pressure, to give 3-cyclopentyloxy-4-difluoromethoxybenzoic acid (0.47 g), in the form of a white solid, m.p. 126-128° C.

Workup

  1. customthat is prepared
  2. temperatureit is heated
  3. temperatureat reflux for 3 hours
  4. customMethanol is evaporated off under reduced pressure
  5. dissolutionthe residue is dissolved in water (40 mL)
  6. washThe solution is washed with diethyl ether (40 mL)
  7. extractionextracted with ethyl acetate (3×40 mL)
  8. dry with materialThe combined ethyl acetate extracts are dried over magnesium sulfate
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-464210eea1c341848be0791471c12421
Source dataset
uspto-grants-2001_07
Patent number
US06255326B1

Reaction notes

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