Sulfamic Acid → 3-(Cyclopentyloxy)-4-methoxybenzoic acid

HRID 976659Notes

Reaction equation

HRID 976659 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][C:14]=2[O:15][CH3:16])[CH:10]=[O:11])[CH2:5][CH2:4][CH2:3][CH2:2]1.S(=O)(=O)([OH:19])N.Cl([O-])=O.[Na+]>C(O)(=O)C.O>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][C:14]=2[O:15][CH3:16])[C:10]([OH:19])=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 3

HCID 5987Sulfamic AcidHCID 27358933-Cyclopentyloxy-4-methoxybenzaldehydeHCID 23668197Sodium Chlorite

Product 1

HCID 27793233-(Cyclopentyloxy)-4-methoxybenzoic acidYield 90.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Conditions

Temperature
20 °C

Procedure

A suspension of 3-cyclopentyloxy-4-methoxybenzaldehyde (19.8 g, 0.09 mole) and sulfamic acid (11.4 g, 0.12 mole) in 80% acetic acid (155 mL) was stirred while a solution of 80% sodium chlorite in water (43 mL) was slowly added. The reaction temperature was maintained at about 20° C. with an ice bath. The resulting yellow mixture was stirred at 20° C. for 1.5 hours, diluted with water (160 mL) and then stirred for 10 minutes. A white solid was isolated by filtration, washed with water and dried in a vacuum oven at 60° C. to provide 19.3 g of 3-cyclopentyloxy-4-methoxybenzoic acid.

Workup

  1. additionwas slowly added
  2. stirringstirred for 10 minutes
  3. customA white solid was isolated by filtration
  4. washwashed with water
  5. customdried in a vacuum oven at 60° C.

Sources & evidence

ORD record
ord-53c0f359728d49708495788934087ea7
Source dataset
uspto-grants-1997_03
Patent number
US05612377

Reaction notes

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