Lithium Hydroxide → 3-(1-Cyanocyclopropyl)benzoic acid

HRID 1184844Notes

Reaction equation

HRID 1184844 reaction equation
[C:1]([C:3]1([C:6]2[CH:7]=[C:8]([CH:13]=[CH:14][CH:15]=2)[C:9]([O:11]C)=[O:10])[CH2:5][CH2:4]1)#[N:2].[OH-].[Li+]>C1COCC1.CO.O.O>[C:1]([C:3]1([C:6]2[CH:7]=[C:8]([CH:13]=[CH:14][CH:15]=2)[C:9]([OH:11])=[O:10])[CH2:4][CH2:5]1)#[N:2]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 57441038Methyl 3-(1-cyanocyclopropyl)benzoate

Product 1

HCID 574410393-(1-Cyanocyclopropyl)benzoic acidYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

A solution of 33 (1.56 g, 7.75 mmol) in 25 mL of THF/MeOH/H2O (3/1/1) was added lithium hydroxide (613 mg, 25.6 mmol) in water (5 mL). The mixture was stirred overnight at rt. Concentrated in vacuo and the resulting solution was acidified with 1N HCl (until pH=1). The resulting precipitate was collected and washed with water and dried to give 3-(1-cyanocyclopropyl)benzoic acid 34 (1.19 g, 82%). NMR (400 MHz, CDCl3) 1.49 (m, 2H), 1.81 (m, 2H), 7.50 (t, J=7.8 Hz, 1H), 7.67 (m, 1H), 7.94 (m, 1H), 8.05 (m, 1H).

Workup

  1. concentrationConcentrated in vacuo
  2. customThe resulting precipitate was collected
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-3c251414d0544e818b6996c07db10e99
Source dataset
uspto-grants-2014_03
Patent number
US08669256B2

Reaction notes

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