Hydrochloric Acid → 3-tert-Butyl-5-cyanobenzoic acid

HRID 1640142Notes

Reaction equation

HRID 1640142 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([C:15]#[N:16])[CH:14]=1)[C:8]([O:10]C)=[O:9])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl>CO.O>[C:1]([C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([C:15]#[N:16])[CH:14]=1)[C:8]([OH:10])=[O:9])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24729630Methyl 3-tert-butyl-5-cyanobenzoate

Product 1

HCID 247296293-tert-Butyl-5-cyanobenzoic acidYield 124.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 3-tert-butyl-5-cyanobenzoate (8.8 g, 0.0360 mol) in MeOH (76 mL) was added a solution of NaOH (2.0 g, 0.050 mol) in water (15 mL). The mixture was allowed to stir at rt for 2.5 h and then acidified with 1N HCl. The mixture was concentrated to remove methanol and the residue was extracted with EtOAc. The organic solutions were combined, washed with 1NHCl and brine, dried over Na2SO4, filtered, and concentrated to a small volume. Hexane was added and the product precipitated. The solid was filtered, washed with hexanes and dried to give 3-tert-butyl-5-cyanobenzoic acid (9.1 g, 73%). 1H NMR (400 MHz, d6-DMSO) δ: 8.19 (m, 1H), 8.13 (m, 1H), 8.10 (m, 1H), and 1.32 (s, 9H). LCMS: ES− 202.2.

Workup

  1. concentrationThe mixture was concentrated
  2. customto remove methanol
  3. extractionthe residue was extracted with EtOAc
  4. washwashed with 1NHCl and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to a small volume
  8. additionHexane was added
  9. customthe product precipitated
  10. filtrationThe solid was filtered
  11. washwashed with hexanes
  12. customdried

Sources & evidence

ORD record
ord-246fadf7bfbe4dd8b8c616ad240a29b1
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

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