Hydrochloric Acid → 3-(2-Cyano-2-methylpropyl)benzoic acid

HRID 1800758Notes

Reaction equation

HRID 1800758 reaction equation
[C:1]([C:3]([CH3:16])([CH3:15])[CH2:4][C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][CH:14]=1)[C:8]([O:10]C)=[O:9])#[N:2].O1CCCC1.[OH-].[Na+].Cl>CO>[C:1]([C:3]([CH3:16])([CH3:15])[CH2:4][C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][CH:14]=1)[C:8]([OH:10])=[O:9])#[N:2]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 68418604HCID 68418604, compound

Product 1

HCID 684167713-(2-Cyano-2-methylpropyl)benzoic acidYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of methyl 3-(2-cyano-2-methylpropyl)benzoate (260 mg, 1.20 mmol) in methanol (6 mL)/tetrahydrofuran (2 mL) was added 2N aqueous sodium hydroxide solution (1.20 mL, 2.39 mmol), and the mixture was stirred at 60° C. for 2 hr. The reaction mixture was neutralized with 6N hydrochloric acid (600 μL), 1N hydrochloric acid (30 mL) was added, and the mixture was extracted with ethyl acetate (30 mL, 10 mL). The combined organic layer was washed with saturated brine (5 mL), and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure to give the title compound (230 mg, 95%) as a white solid.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate (30 mL, 10 mL)
  3. washThe combined organic layer was washed with saturated brine (5 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe insoluble material was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-11461a074ef54da0ba40ae26b38b8c33
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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