Sulfamic Acid → Benzoic acid, 4-methoxy-3-[(methylsulfonyl)oxy]-

HRID 1776577Notes

Reaction equation

HRID 1776577 reaction equation
[CH3:1][S:2]([O:5][C:6]1[CH:11]=[C:10]([CH:12]=[O:13])[CH:9]=[CH:8][C:7]=1[O:14][CH3:15])(=[O:4])=[O:3].S(=O)(=O)([OH:18])N.Cl([O-])=O.[Na+]>C(O)(=O)C.O>[CH3:15][O:14][C:7]1[CH:8]=[CH:9][C:10]([C:12]([OH:18])=[O:13])=[CH:11][C:6]=1[O:5][S:2]([CH3:1])(=[O:4])=[O:3]

Participants

6

Reactant 3

HCID 5987Sulfamic AcidHCID 23668197Sodium ChloriteHCID 588275424-Methoxy-3-[(methylsulfonyl)oxy]benzaldehyde

Product 1

HCID 11954874Benzoic acid, 4-methoxy-3-[(methylsulfonyl)oxy]-Yield 268.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

5-formyl-2-methoxyphenyl methanesulfonate (3.3 g, 14 mmol) was dissolved in acetic acid (50 ml) and sulfamic acid (500 mg, 5.15 mmol) was added. Sodium chlorite (3 g, 33.2 mmol) was dissolved in H2O (20 ml) and added dropwise. The reaction was stirred at RT overnight, then the precipitate was filtered and washed with HCl 1 M, MeOH and dried in the vacuum oven, to give 3.4 g of the desired product (Yield: 99%).

Workup

  1. additionadded dropwise
  2. filtrationthe precipitate was filtered
  3. washwashed with HCl 1 M, MeOH
  4. customdried in the vacuum oven

Sources & evidence

ORD record
ord-3db6dca764f045fab1da95f9dbb140db
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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