Sulfamic Acid → 2-Methoxy-6-(3-methoxyphenyl)-1-naphthoic acid

HRID 1035593Notes

Reaction equation

HRID 1035593 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=3)[CH:9]=2)[C:4]=1[CH:21]=[O:22].NS(O)(=O)=[O:25].Cl[O-].[Na+]>O.CC(C)=O>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=3)[CH:9]=2)[C:4]=1[C:21]([OH:25])=[O:22]

Participants

6

Reactant 3

HCID 5987Sulfamic AcidHCID 23665760Sodium HypochloriteHCID 59443478HCID 59443478, compound

Product 1

HCID 594434812-Methoxy-6-(3-methoxyphenyl)-1-naphthoic acid

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

200 mg of the compound 2-methoxy-6-(3-methoxyphenyl)-1-naphthaldehyde (0.68 mmol, 1 eq) is dissolved in a mixture of 8 ml of water and 17 ml of acetone. To the cooled reaction mixture, amidosulfonic acid (H2NSO3H) (1.51 mmol, 2.21 eq) and sodium hypochlorite (0.78 mmol, 1.14 eq) are added. After stirring for 30 min, the acetone is removed in vacuum on a rotary evaporator, and dichloromethane is added. The organic and aqueous phases are separated, and the organic phase is washed three times with saturated sodium chloride solution. After drying and concentrating the organic phase on a rotary evaporator, the desired product was obtained as a yellow solid in quantitative yield (209 mg).

Workup

  1. additionare added
  2. customthe acetone is removed in vacuum on a rotary evaporator, and dichloromethane
  3. additionis added
  4. customThe organic and aqueous phases are separated
  5. washthe organic phase is washed three times with saturated sodium chloride solution
  6. customAfter drying
  7. concentrationconcentrating the organic phase
  8. customon a rotary evaporator

Sources & evidence

ORD record
ord-2bfff05418004227ae9e8e6e5b0b2ff1
Source dataset
uspto-grants-2013_10
Patent number
US08546392B2

Reaction notes

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