Potassium Carbonate → HCID 21187897, compound

HRID 1383551Notes

Reaction equation

HRID 1383551 reaction equation
[F:1][C:2]1([F:20])[C:5]([O:6][C:7]2[CH:8]=[C:9]([CH:14]=[CH:15][C:16]=2[O:17][CH3:18])[C:10]([O:12]C)=[O:11])=[CH:4][C:3]1=[CH2:19].C(=O)([O-])[O-].[K+].[K+]>CO.O>[F:1][C:2]1([F:20])[C:5]([O:6][C:7]2[CH:8]=[C:9]([CH:14]=[CH:15][C:16]=2[O:17][CH3:18])[C:10]([OH:12])=[O:11])=[CH:4][C:3]1=[CH2:19]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 21187923HCID 21187923, compound

Product 1

HCID 21187897HCID 21187897, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

A solution of methyl 3-(4,4-difluoro-3-methylenecyclobut-1-enyloxy)-4-methoxybenzoate (1.39 g) in methanol (22 mL) is treated with a solution of potassium carbonate (0.83 g) in water (8 mL) and the solution is heated at 60-70° C. for 8 hours, cooled and evaporated. The residue is dissolved in water (30 mL), extracted with diethyl ether (50 mL) and acidified to pH 4 by treatment with glacial acetic acid. The precipitated solid is extracted with ethyl acetate (2×75 mL). The combined organic extracts are dried over magnesium sulfate and concentrated, to give 3-(4,4-difluoro-3-methylene-cyclobut-1-enyloxy)-4-methoxybenzoic acid, in the form of a white solid, m.p. 163-165° C.

Workup

  1. temperaturecooled
  2. customevaporated
  3. dissolutionThe residue is dissolved in water (30 mL)
  4. extractionextracted with diethyl ether (50 mL)
  5. extractionThe precipitated solid is extracted with ethyl acetate (2×75 mL)
  6. dry with materialThe combined organic extracts are dried over magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e1415b85193e4e6ebbd254347bd94901
Source dataset
uspto-grants-2001_07
Patent number
US06255326B1

Reaction notes

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