Hydrochloric Acid → 3-t-Butyl-5-cyano-4-methoxybenzoic acid

HRID 385033Notes

Reaction equation

HRID 385033 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([C:17]#[N:18])[C:14]=1[O:15][CH3:16])[C:8]([O:10]C)=[O:9])([CH3:4])([CH3:3])[CH3:2].O1CCCC1.O.[OH-].[Li+].Cl>CO.O>[C:1]([C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([C:17]#[N:18])[C:14]=1[O:15][CH3:16])[C:8]([OH:10])=[O:9])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 68108985Methyl 3-t-butyl-5-cyano-4-methoxybenzoate

Product 1

HCID 681088003-t-Butyl-5-cyano-4-methoxybenzoic acidYield 84.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Methyl 3-t-butyl-5-cyano-4-methoxybenzoate (1.48 g) was dissolved in methanol (20 ml), tetrahydrofuran (5 mL) and water (5 mL), and lithium hydroxide monohydrate (753 mg) was added to the solution, and then the mixture was stirred at room temperature for 2 hours. To the reaction solution, 10% hydrochloric acid was added, and then the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound (1.18 g) as a pale yellow crystal.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-743a64905ea2465aa1aa895424e54508
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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