Water → HCID 21187833, compound

HRID 1870414Notes

Reaction equation

HRID 1870414 reaction equation
C(=O)([O-])[O-].[K+].[K+].O.[CH:8]1([O:13][C:14]2[CH:15]=[C:16]([CH:21]=[CH:22][C:23]=2[O:24][C:25]([F:28])([F:27])[F:26])[C:17]([O:19]C)=[O:18])[CH2:12][CH2:11][CH2:10][CH2:9]1>CO>[CH:8]1([O:13][C:14]2[CH:15]=[C:16]([CH:21]=[CH:22][C:23]=2[O:24][C:25]([F:26])([F:27])[F:28])[C:17]([OH:19])=[O:18])[CH2:9][CH2:10][CH2:11][CH2:12]1

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 21187847HCID 21187847, compound

Product 1

HCID 21187833HCID 21187833, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium carbonate (0.43 g) and water (2 mL) are added to a solution of methyl 3-cyclopentyloxy-4-trifluoromethoxybenzoate (0.78 g) in methanol (10 mL) and the mixture is heated under reflux for 2 hours. Methanol is evaporated off under reduced pressure, and the crude material is partitioned between water (75 mL) and ethyl acetate (75 mL). The organic layer is separated, and the aqueous layer is acidified with hydrochloric acid (2 N) and extracted with ethyl acetate (2×75 mL). The combined organic extracts are dried over magnesium sulfate and evaporated under reduced pressure, to give 3-cyclopentyloxy-4-trifluoromethoxybenzoic acid (0.53 g), in the form of a white solid, m.p. 116-118° C. [NMR (CDCl3): 7.72(d,1H,J=2 Hz); 7.7(dd,1H,J=8 Hz, 2 Hz); 7.3(d,1H,J=8 Hz);4.9(m,1H);2.0-1.6(m,8H)].

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 2 hours
  3. customMethanol is evaporated off under reduced pressure
  4. customthe crude material is partitioned between water (75 mL) and ethyl acetate (75 mL)
  5. customThe organic layer is separated
  6. extractionextracted with ethyl acetate (2×75 mL)
  7. dry with materialThe combined organic extracts are dried over magnesium sulfate
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-8fae29cd2e2c4db5a032c21f9d1607bb
Source dataset
uspto-grants-2000_08
Patent number
US06096768

Reaction notes

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