Lithium Hydroxide → 3-(2-Cyanopropan-2-yl)benzoic acid

HRID 1184813Notes

Reaction equation

HRID 1184813 reaction equation
[C:1]([C:3]([C:6]1[CH:7]=[C:8]([CH:13]=[CH:14][CH:15]=1)[C:9]([O:11]C)=[O:10])([CH3:5])[CH3:4])#[N:2].[OH-].[Li+]>C1COCC1.CO.O>[C:1]([C:3]([C:6]1[CH:7]=[C:8]([CH:13]=[CH:14][CH:15]=1)[C:9]([OH:11])=[O:10])([CH3:5])[CH3:4])#[N:2]

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 57441035Methyl 3-(2-cyanopropan-2-yl)benzoate

Product 1

HCID 571495383-(2-Cyanopropan-2-yl)benzoic acidYield 1,854.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 3-(2-cyanopropan-2-yl)benzoate 2 (72 g, 5.9 mmol) in THF (900 mL), MeOH (300 mL) and water 300 (mL) was treated with lithium hydroxide (47.6 g, 1.13 mol). The mixture was stirred overnight at rt. Concentrated to ±300 mL in vacuo and the resulting solution was acidified with 1N HCl solution. The resulting white precipitate was collected, washed with water and dried. Purification by column chromatography (5% methanol in CH2Cl2) gave pure 3-(2-cyanopropan-2-yl)benzoic acid 3 (20.7 g, 31%). 1H-NMR (400 MHz, CDCl3) 1.78 (s, 6H), (t, J=7.5 Hz, 1H), 7.80 (m, 1H), 8.09 (m, 1H), 8.20 (m, 1H).

Workup

  1. concentrationConcentrated
  2. customThe resulting white precipitate was collected
  3. washwashed with water
  4. customdried
  5. customPurification by column chromatography (5% methanol in CH2Cl2)

Sources & evidence

ORD record
ord-d47a563f46fa4e68b577379b85a76b5f
Source dataset
uspto-grants-2014_03
Patent number
US08669256B2

Reaction notes

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