Hydrochloric Acid → 2-(4-Fluorophenyl)cyclopropane-1-carboxylic acid

HRID 853026Notes

Reaction equation

HRID 853026 reaction equation
C([O:3][C:4]([CH:6]1[CH2:8][CH:7]1[C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1)=[O:5])C.O.[Li].CO.Cl>O>[F:15][C:12]1[CH:11]=[CH:10][C:9]([CH:7]2[CH2:8][CH:6]2[C:4]([OH:5])=[O:3])=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 232682772-(4-fluoro-phenyl)-cyclopropanecarboxylic Acid Ethyl EsterHCID 57448853Lithium monohydrate

Product 1

HCID 218646542-(4-Fluorophenyl)cyclopropane-1-carboxylic acidYield 109.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

In a round flask was charged with 2-(4-fluoro-phenyl)-cyclopropanecarboxylic acid ethyl ester (1700 mg, 8.16 mmol), lithium monohydrate (1370 mg, 32.7 mmol), methanol (25 mL) and water (10 mL). The mixture was heated at 80° C. for 2 hours. The reaction mixture was rotavaped. The residue was neutralized with 4N hydrochloric acid and extracted with dichloromethane. The dichloromethane layer was washed with brine, dried over sodium sulfate and evaporated to give 1.61 grams of white solid as desired product. LC-MS m/e 179 (MH−).

Workup

  1. extractionextracted with dichloromethane
  2. washThe dichloromethane layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-e241415c28f1486b8f59b99aaf1da2ad
Source dataset
uspto-grants-2007_08
Patent number
US07253285B2

Reaction notes

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