Lithium hydroxide, monohydrate → 1-(Phenylcarbamoyl)cyclopropanecarboxylic acid

HRID 476366Notes

Reaction equation

HRID 476366 reaction equation
[C:1]1([NH:7][C:8]([C:10]2([C:13]([O:15]C)=[O:14])[CH2:12][CH2:11]2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[OH-].[Li+]>C1COCC1.O>[C:1]1([NH:7][C:8]([C:10]2([C:13]([OH:15])=[O:14])[CH2:11][CH2:12]2)=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 66605339Methyl 1-(phenylcarbamoyl)cyclopropanecarboxylate

Product 1

HCID 190968711-(Phenylcarbamoyl)cyclopropanecarboxylic acidYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 1-(phenylcarbamoyl)cyclopropanecarboxylate (0.607 g, 2.77 mmol) was dissolved in a mixture of THF (3.5 mL) and water (3.50 mL), lithium hydroxide monohydrate (0.349 g, 8.31 mmol) was added, and the mixture was stirred at room temperature for 1 hour. The THF was removed under reduced pressure and additional water (20 mL) was added. The solution was acidified to ˜pH 4 with 2 M HCl and the off white solid that precipitated was collected by suction filtration and washed with additional water to give 1-(phenylcarbamoyl)cyclopropanecarboxylic acid (0.482 g, 85% yield). MS (ESI) m/z: 206.0 (M+H+)

Workup

  1. additionwas added
  2. customThe THF was removed under reduced pressure and additional water (20 mL)
  3. additionwas added
  4. customthe off white solid that precipitated
  5. filtrationwas collected by suction filtration
  6. washwashed with additional water

Sources & evidence

ORD record
ord-9f4855de4ee6436b908f900da7b01e6d
Source dataset
uspto-grants-2014_01
Patent number
US08637672B2

Reaction notes

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