Sulfamic Acid → 7-Methoxy-2-methylbenzo[b]furan-4-carboxylic acid

HRID 548968Notes

Reaction equation

HRID 548968 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[O:9][C:10]([CH3:12])=[CH:11][C:7]=2[C:6]([CH:13]=[O:14])=[CH:5][CH:4]=1.S(=O)(=O)([OH:17])N.Cl([O-])=O.[Na+]>CC(C)=O.O>[CH3:1][O:2][C:3]1[C:8]2[O:9][C:10]([CH3:12])=[CH:11][C:7]=2[C:6]([C:13]([OH:17])=[O:14])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 5987Sulfamic AcidHCID 110415447-Methoxy-2-methyl-1-benzofuran-4-carbaldehydeHCID 23668197Sodium Chlorite

Product 1

HCID 220095237-Methoxy-2-methylbenzo[b]furan-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a well stirred solution of 7-methoxy-2-methylbenzo[b]furan-4-carboxaldehyde (from step 3) (4.0 g, 21.05 mmol) in acetone (40.0 mL) was added a solution of sulphamic acid (2.4 g, 25.26 mmol) in water (10.0 mL) followed by addition of a solution of sodium chlorite (2.8 g, 31.57 mmol) at 5-10° C. Ice cold water (250 mL) was added to reaction mixture and the product separated was filtered and dried at 60-70° C. to give intermediate-4 (3.2 g) as white solid.

Workup

  1. customthe product separated
  2. filtrationwas filtered
  3. customdried at 60-70° C.
  4. customto give intermediate-4 (3.2 g) as white solid

Sources & evidence

ORD record
ord-228d7fd4e84c49fbbbc7a9f75ebaba6f
Source dataset
uspto-grants-2011_05
Patent number
US07943634B2

Reaction notes

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