Sulfamic Acid → 3-Methoxy-4-(2-trifluoromethylphenyl)benzoic acid

HRID 1830064Notes

Reaction equation

HRID 1830064 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH:9]=[O:10])[CH:6]=[CH:5][C:4]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]([F:20])([F:19])[F:18].S(=O)(=O)([OH:23])N.Cl([O-])=O.[Na+].CCCCCC>O1CCCC1.O>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]([OH:23])=[O:10])[CH:6]=[CH:5][C:4]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]([F:18])([F:19])[F:20]

Participants

7

Reactant 4

HCID 5987Sulfamic Acid2×HCID 8058HexaneHCID 219478512-Methoxy-2'-trifluoromethyl-[1,1'-biphenyl]-4-carboxaldehydeHCID 23668197Sodium Chlorite2×

Product 1

HCID 219477213-Methoxy-4-(2-trifluoromethylphenyl)benzoic acidYield 83.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The 2-methoxy-2′-trifluoromethyl-[1,1′-biphenyl]-4-carboxaldehyde of Step B (0.95 g, 3.41 mmol) and sulfamic acid (0.43 g, 4.43 mmol) were dissolved in a mixture of tetrahydrofuran and water (1:1, v/v, 30 mL). Sodium chlorite (0.31 g, 4.43 mmol) was added under stirring, and the solution turned yellow. After 30 minutes, additional sodium chlorite (0.1 g) and sulfamic acid were added, and the solution stirred an additional hour. The solution was then concentrated, and the residue partitioned between ethyl acetate and water. The ethyl acetate layer was dried and concentrated to yield an oil, which solidified upon trituration with hexane to provide the title compound (0.84 g) as a yellow solid, which was used in the next step.

Workup

  1. stirringthe solution stirred an additional hour
  2. concentrationThe solution was then concentrated
  3. customthe residue partitioned between ethyl acetate and water
  4. dry with materialThe ethyl acetate layer was dried
  5. concentrationconcentrated
  6. customto yield an oil, which

Sources & evidence

ORD record
ord-31ad557a63ee4cc2b7976bf1ce6ff847
Source dataset
uspto-grants-2006_06
Patent number
US07064120B2

Reaction notes

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