Benzoic Acid → (S)-(+)-3-Cyano-4-(2-methylbutyloxy)benzoic acid

HRID 651307Notes

Reaction equation

HRID 651307 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][C@@H:12]([CH3:15])[CH2:13][CH3:14])=[C:6]([CH:9]=1)[C:7]#[N:8].C([Li])CCC.[Li+].[C:22]([O-:30])(=[O:29])C1C=CC=CC=1.C(O)(=O)C1C=CC=CC=1>O.C(O)(=O)C.C1COCC1>[C:7]([C:6]1[CH:9]=[C:2]([CH:3]=[CH:4][C:5]=1[O:10][CH2:11][C@@H:12]([CH3:15])[CH2:13][CH3:14])[C:22]([OH:30])=[O:29])#[N:8]

Participants

8

Reactant 4

HCID 243Benzoic AcidHCID 2724073Lithium BenzoateHCID 53787839(S)-(+)-5-Bromo-2-(2-methylbutyloxy)benzonitrileHCID 178418339Butyllithium2×

Product 1

HCID 54501986(S)-(+)-3-Cyano-4-(2-methylbutyloxy)benzoic acid

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Quantities: compound 41 (5.00 g, 0.016 mol), n-butyllithium (2.5 M, 7.2 ml, 0.018 mol), THF (100 ml). The experimental procedure was as described for compound 36 except that the n-butyllithium was added between −90° C. and −100° C. Acidification of the resultant benzoic acid lithium salt was achieved by boiling with glacial acetic acid. The benzoic acid was crashed out of solution by diluting with a large volume of water, the resultant product was washed with water (until acid-free) and then purified as described for compound 36 to leave an off-white semi-solid.

Workup

  1. additionwas added between −90° C. and −100° C
  2. washthe resultant product was washed with water (until acid-free)
  3. custompurified
  4. customto leave an off-white semi-solid

Sources & evidence

ORD record
ord-e4ba67e39f2e435fb18a7ea06a1fcc92
Source dataset
uspto-grants-2001_08
Patent number
US06278028B1

Reaction notes

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