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

HRID 1489695Notes

Reaction equation

HRID 1489695 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.[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 5360545Sodium

Product 1

HCID 27793233-(Cyclopentyloxy)-4-methoxybenzoic acidYield 86%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Conditions

Temperature
20 °C

Procedure

A solution of 3-cyclopentyloxy-4-methoxybenzaldehyde (66 g) and sulfamic acid (39.6 g) in glacial acetic acid (500 mL) is treated dropwise during 1 hour with a solution of sodium chicrite (35 g) in water (150 mL). The mixture is stirred at 20° C. during 1 hour and then it is treated with water (500 mL) dropwise during 30 minutes. The resulting solid is filtered, washed with water and dried, to give 3-cyclopentyloxy-4-methoxybenzoic acid (60.9 g) in the form of white crystals [Elemental analysis: C,65.8; H,6.7%; calculated: C,66.1; H,6.8%].

Workup

  1. filtrationThe resulting solid is filtered
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-a5a2e2eca1b2403fb73a17c645a71266
Source dataset
uspto-grants-1997_10
Patent number
US05679696

Reaction notes

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