4-Hydroxybenzenesulfonic acid → Sodium 4-(2-cyclopentylethoxy)benzenesulfonate

HRID 380579Notes

Reaction equation

HRID 380579 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([OH:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[OH-].[Na+:13].Br[CH2:15][CH2:16][CH:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1>O.C(O)(C)C>[CH:17]1([CH2:16][CH2:15][O:1][C:2]2[CH:7]=[CH:6][C:5]([S:8]([O-:11])(=[O:9])=[O:10])=[CH:4][CH:3]=2)[CH2:21][CH2:20][CH2:19][CH2:18]1.[Na+:13]

Participants

6

Reactant 3

HCID 47654-Hydroxybenzenesulfonic acidHCID 14798Sodium HydroxideHCID 12711948(2-Bromoethyl)cyclopentane

Product 1

HCID 23697515Sodium 4-(2-cyclopentylethoxy)benzenesulfonate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

A solution of 4-hydroxybenzenesulfonic acid (6.5 grams, 28.2 mmole) and sodium hydroxide (2.2 grams, 55 mmole) in water (15 mL) was mixed with a solution of 2-(bromoethyl)cyclopentane (15.0 grams, 84.7 mmole) in isopropanol (40 mL) and the resulting mixture was heated at reflux for 2 days. The isopropanol was removed by evaporation under vaccuum. The titled compound, 4.7 grams (57%), was collected by filtration washing with isopropanol.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 2 days
  3. customThe isopropanol was removed by evaporation under vaccuum
  4. filtrationThe titled compound, 4.7 grams (57%), was collected by filtration
  5. washwashing with isopropanol

Sources & evidence

ORD record
ord-2ed9b92defbf4751a925c4a17b2d2411
Source dataset
uspto-grants-2001_10
Patent number
US06303636B1

Reaction notes

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