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

HRID 1667849Notes

Reaction equation

HRID 1667849 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-f62d6d32a7ab418ea3c9c2e48f1e1620
Source dataset
uspto-grants-2011_10
Patent number
US08044049B2

Reaction notes

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