Hydrochloric Acid → 3-Cyanoethylbenzoic acid

HRID 1800755Notes

Reaction equation

HRID 1800755 reaction equation
[C:1]([CH2:3][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]([CH2:3][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 20209683HCID 20209683, compound

Product 1

HCID 221747763-Cyanoethylbenzoic acidYield 96.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of methyl 3-(2-cyanoethyl)benzoate (169 mg, 893 μmol) in methanol (3 mL)/tetrahydrofuran (1 mL) was added 2N aqueous sodium hydroxide solution (893 μL, 1.79 mmol), and the mixture was stirred at 60° C. for 4 hr. The reaction mixture was neutralized with 6N hydrochloric acid (500 μL), 1N hydrochloric acid (15 mL) was added, and the mixture was extracted with ethyl acetate (20 mL, 5 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 (151 mg, 96%) as a white solid.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate (20 mL, 5 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-4a9e872a672b40878261188a52c8a773
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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