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

HRID 2215143Notes

Reaction equation

HRID 2215143 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 9, 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 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-3d525d48f0d94559a016a63d16b0ca5e
Source dataset
uspto-grants-2006_09
Patent number
US07109193B2

Reaction notes

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