Lithium hydroxide, monohydrate → 3-(1-Cyano-2-cyclopropyl-1-methylethyl)benzoic acid

HRID 2391160Notes

Reaction equation

HRID 2391160 reaction equation
[C:1]([C:3]([C:9]1[CH:10]=[C:11]([CH:16]=[CH:17][CH:18]=1)[C:12]([O:14]C)=[O:13])([CH3:8])[CH2:4][CH:5]1[CH2:7][CH2:6]1)#[N:2].O.[OH-].[Li+]>O1CCCC1.CO.O>[C:1]([C:3]([C:9]1[CH:10]=[C:11]([CH:16]=[CH:17][CH:18]=1)[C:12]([OH:14])=[O:13])([CH3:8])[CH2:4][CH:5]1[CH2:7][CH2:6]1)#[N:2]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 57441044HCID 57441044, compound

Product 1

HCID 574410453-(1-Cyano-2-cyclopropyl-1-methylethyl)benzoic acidYield 67.6%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a solution of methyl 3-(1-cyano-2-cyclopropyl-1-methylethyl)benzoate (120 mg, 0.49 mmol) in tetrahydrofuran/methanol/water (=3.0 mL/1.0 mL/1.0 mL) was added lithium hydroxide monohydrate (40 mg, 0.99 mmol), and the reaction mixture was stirred at room temperature for 4 hr. The mixture was concentrated under reduced pressure, and the obtained aqueous solution was adjusted to pH 5 by adding 1N hydrochloric acid. The mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=50/50→100/0) to give the title compound (76 mg, 66%) as a colorless oil.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additionby adding 1N hydrochloric acid
  3. concentrationThe mixture was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=50/50→100/0)

Sources & evidence

ORD record
ord-adb69247544a4e348bb3e7603c7839d4
Source dataset
uspto-grants-2012_09
Patent number
US08273741B2

Reaction notes

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