Sulfamic Acid → 3-Methoxy-4-(methoxycarbonyl)benzoic acid

HRID 508809Notes

Reaction equation

HRID 508809 reaction equation
[CH:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([O:13][CH3:14])[CH:4]=1)=[O:2].S(=O)(=O)([OH:17])N.Cl([O-])=O.[Na+]>CC(C)=O>[CH3:14][O:13][C:5]1[CH:4]=[C:3]([CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8])[C:1]([OH:17])=[O:2]

Participants

5

Reactant 3

HCID 5987Sulfamic AcidHCID 18510332Methyl 4-formyl-2-methoxybenzoateHCID 23668197Sodium Chlorite

Product 1

HCID 123983053-Methoxy-4-(methoxycarbonyl)benzoic acidYield 123.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a cold solution of methyl 4-formyl-2-methoxybenzoate (6.0 g, 7.73 mmol) in acetone (50 mL) was added aqueous sulphamic acid solution (4.5 g, 11.59 mmol) and aqueous sodium chlorite solution (4.04 g, 11.59 mmol) at 0-5° C. The reaction mixture was stirred at RT for 3-4 h. Excess of solvent was removed under vacuum. The obtained residue was diluted with water and basified with saturated sodium bicarbonate solution. The aqueous layer was washed with diethyl ether to remove organic impurities and the obtained aqueous layer was again acidified with conc.HCl. The solid obtained was filtered and suck dried to afford 2.00 g of desired product. 1H NMR (300 MHz, DMSO d6): δ 3.80 (s, 3H), 3.87 (s, 3H), 7.55-7.59 (m, 2H), 7.70 (d, J=7.8 Hz, 1H), 13.37 (s, 1H); MS (m/z): 210.97 (M+H)+.

Workup

  1. customExcess of solvent was removed under vacuum
  2. additionThe obtained residue was diluted with water and basified with saturated sodium bicarbonate solution
  3. washThe aqueous layer was washed with diethyl ether
  4. customto remove organic impurities
  5. customThe solid obtained
  6. filtrationwas filtered
  7. customsuck dried

Sources & evidence

ORD record
ord-eb8cded598334fb09a9480d8e1edc17c
Source dataset
uspto-grants-2015_08
Patent number
US09096545B2

Reaction notes

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