Methanol → 2-(3-Fluoro-4-methoxyphenyl)cyclopropane-1-carboxylic acid

HRID 62907Notes

Reaction equation

HRID 62907 reaction equation
C([O:3][C:4]([CH:6]1[CH2:8][CH:7]1[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([F:17])[CH:10]=1)=[O:5])C.CO.O.[OH-].[Na+]>C1COCC1>[F:17][C:11]1[CH:10]=[C:9]([CH:7]2[CH2:8][CH:6]2[C:4]([OH:5])=[O:3])[CH:14]=[CH:13][C:12]=1[O:15][CH3:16]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 14798Sodium HydroxideHCID 58566289Ethyl 2-(3-fluoro-4-methoxyphenyl)cyclopropanecarboxylate

Product 1

HCID 211905602-(3-Fluoro-4-methoxyphenyl)cyclopropane-1-carboxylic acidYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

After 2-(3-fluoro-4-methoxy-phenyl)-cyclopropane carboxylic acid ethyl ester (1.15 g, 4.83 mmol) was dissolved in THF (6 mL), methyl alcohol (1 mL) and water (1 mL), an excess amount of sodium hydroxide was added, and then the mixture was stirred at room temperature for 4 hours. After the termination of the reaction, the reactant was concentrated under reduced pressure, and 1N HCl was added to adjust the pH of the solution to 2. The organic layer obtained by the extraction with ethyl acetate was separated, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain the title compound (0.985 g, 97%).

Workup

  1. customAfter the termination of the reaction
  2. concentrationthe reactant was concentrated under reduced pressure, and 1N HCl
  3. additionwas added
  4. customThe organic layer obtained by the extraction with ethyl acetate
  5. customwas separated
  6. dry with materialdried with anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f4817615211a4d11b877cd0e0d90072d
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

Loading…