Methane → Benzoic Acid

HRID 881023Notes

Reaction equation

HRID 881023 reaction equation
[C:1]([O-:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na+].C>O>[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 297MethaneHCID 517055Sodium Benzoate

Product 1

HCID 243Benzoic Acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Alternatively to a solution of 5.0 g of the compound prepared in Example 4 in 100 mL of water was added 2.2 g of sodium benzoate. The mixture was heated on a steam bath until homogeneous. Charcoal (approximately 2 g) was added and this mixture was filtered through Celite® washing with 20 mL of water. Crystallization began immediately. After cooling for 2 h, the solids were collected and washed with water. After drying the solids for 3 days in a vacuum oven at 50° C., 3.9 g (67%) was collected. 1H NMR confirmed the salt as a 1:1 ratio of benzoic acid and methyl (2R,3R)-2-{3-[amino(imino)methyl]benzyl}-3-{[4-(1-oxidopyridin-4-yl)benzoyl]amino}butanoate.

Workup

  1. temperatureThe mixture was heated on a steam bath until homogeneous
  2. filtrationthis mixture was filtered through Celite®
  3. washwashing with 20 mL of water
  4. customCrystallization
  5. temperatureAfter cooling for 2 h
  6. customthe solids were collected
  7. washwashed with water
  8. customAfter drying the solids for 3 days in a vacuum oven at 50° C.
  9. custom3.9 g (67%) was collected

Sources & evidence

ORD record
ord-65b7eeb42ad041b8ab819a91a4effd84
Source dataset
uspto-grants-2015_03
Patent number
US08993602B2

Reaction notes

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