Hydrochloric Acid → 3-Cyano-4-isobutylbenzoic acid

HRID 423320Notes

Reaction equation

HRID 423320 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[CH2:13][CH:14]([CH3:16])[CH3:15])[C:6]([O:8]C)=[O:7])#[N:2].[OH-].[Na+].Cl>C(O)C>[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[CH2:13][CH:14]([CH3:16])[CH3:15])[C:6]([OH:8])=[O:7])#[N:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59316752HCID 59316752, compound

Product 1

HCID 222281753-Cyano-4-isobutylbenzoic acidYield 93.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl 3-cyano-4-(2-methylpropyl)benzoate (D31) (233 mg, 1.072 mmol) was dissolved in ethanol (4 ml) and 2M aqueous sodium hydroxide (1 ml, 2 mmol) was added. The reaction was stirred for 1 h. 2M aqueous HCl (10 mL) was added and the mixture extracted with dichloromethane (20 mL+10 mL). The organic phases were isolated and dried by phase separator and combined before the solvent was removed in vacuo to give the title compound as a white solid (203 mg, 0.999 mmol). δH (d6-DMSO, 400 MHz) 13.43 (1H, br. s), 8.29 (1H, d), 8.14 (1H, dd), 7.59 (1H, d), 2.74 (2H, d), 1.96 (1H, m), 0.91 (6H, d). MS (ES): C12H13NO2 requires 203; found 202 (M−H+).

Workup

  1. extractionthe mixture extracted with dichloromethane (20 mL+10 mL)
  2. customThe organic phases were isolated
  3. customdried by phase separator
  4. customwas removed in vacuo

Sources & evidence

ORD record
ord-36cfbfe20b674cff85df2d5af6e15076
Source dataset
uspto-grants-2012_01
Patent number
US08101775B2

Reaction notes

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