Sulfamic Acid → 4-Methoxy-3-(4-methoxy-butyl)-benzoic acid

HRID 1158448Notes

Reaction equation

HRID 1158448 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][C:4]=1[CH2:11][CH2:12][CH2:13][CH2:14][O:15][CH3:16].S(=O)(=O)([OH:19])N.[O-]Cl=O.[Na+]>C(O)(=O)C.O>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]([OH:19])=[O:8])=[CH:5][C:4]=1[CH2:11][CH2:12][CH2:13][CH2:14][O:15][CH3:16]

Participants

6

Reactant 3

HCID 5987Sulfamic Acid2×HCID 23668197Sodium Chlorite2×HCID 862481464-Methoxy-3-(4-methoxy-butyl)-benzaldehyde

Product 1

HCID 595123354-Methoxy-3-(4-methoxy-butyl)-benzoic acid

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent3×

Procedure

To a stirred suspension of 4-methoxy-3-(4-methoxy-butyl)-benzaldehyde (300 mg, 1.35 mmol) and sulfamic acid (176 mg, 1.81 mmol) in 80% acetic acid (2.3 mL) is added dropwise a solution of 80% NaClO2 (127 mg, 1.40 mmol; dissolved in 170 μL of H2O) in water (0.65 mL) over 5 min and by keeping the temperature at 18-20° C. Stirring of the yellow slurry is continued over 3 hrs at 20° C. before adding another aliquot of 80% NaClO2 (151 mg, 1.67 mmol; dissolved in 205 μL of H2O), dissolved in water (0.8 mL), and sulfamic acid (130 mg, 1.34 mmol) in 80% aqueous acetic acid. After stirring overnight, the reaction mixture is diluted by adding water (2.3 mL), the resulting suspension is stirred for 30 min and filtered. The precipitate is dried to give the title product as white solid. TLC, Rf (CH2Cl2/MeOH 98:2)=0.5. MS: 239.0 [M+H]+. 1H-NMR (CD3OD): δ 1.55-1.7 (m, 4H), 2.65 (t, 2H), 3.31 (s, 3H), 3.41 (t, 2H), 3.89 (s, 3H), 4.87 (s, 1H+D2O), 6.98 (m, 1H), 7.78 (s, 1H), 7.87 (m, 1H) ppm.

Workup

  1. customat 18-20° C
  2. stirringAfter stirring overnight
  3. additionthe reaction mixture is diluted
  4. stirringthe resulting suspension is stirred for 30 min
  5. filtrationfiltered
  6. customThe precipitate is dried

Sources & evidence

ORD record
ord-04ad35b598b14e27a5763cd594f51f0e
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

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