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

HRID 548993Notes

Reaction equation

HRID 548993 reaction equation
[CH:1]1([O:6][C:7]2[C:12]3[O:13][C:14]([CH3:16])=[CH:15][C:11]=3[C:10]([CH:17]=[O:18])=[CH:9][CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.S(=O)(=O)([OH:21])N.Cl([O-])=O.[Na+]>CC(C)=O.O>[CH:1]1([O:6][C:7]2[C:12]3[O:13][C:14]([CH3:16])=[CH:15][C:11]=3[C:10]([C:17]([OH:21])=[O:18])=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 3

HCID 5987Sulfamic AcidHCID 23668197Sodium ChloriteHCID 442478827-Cyclopentyloxy-2-methylbenzo[b]furan-4-carboxaldehyde

Product 1

HCID 665925097-Cyclopentyloxy-2-methylbenzo[b]furan-4-carboxylic acidYield 68.3%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a well stirred solution of 7-cyclopentyloxy-2-methylbenzo[b]furan-4-carboxaldehyde (55.0 g, 0.225 moles), sulphamic acid (76.0 g, 0.787 moles) in acetone (600 mL) was added a solution of sodium chlorite (51.0 g, 0.562 moles) in water (150 mL) at 0-5° C. and stirred for 5-6 hrs. Ice cold water (1.0 L) was added to reaction mixture; solid separated was filtered and purified by acid-base technique to get 40.0 g of pure product.

Workup

  1. customsolid separated
  2. filtrationwas filtered
  3. custompurified by acid-base technique

Sources & evidence

ORD record
ord-6753aafa7a7146f19e6cbaca217035c9
Source dataset
uspto-grants-2011_05
Patent number
US07943634B2

Reaction notes

Loading…