4-Hydroxybenzenesulfonic acid → Sodium 4-(3-methylbutoxy)benzenesulfonate

HRID 2288112Notes

Reaction equation

HRID 2288112 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].I[CH2:15][CH2:16][CH:17]([CH3:19])[CH3:18]>O.C(O)(C)C>[CH3:18][CH:17]([CH3:19])[CH2:16][CH2:15][O:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O-:11])(=[O:9])=[O:10])=[CH:4][CH:3]=1.[Na+:13]

Participants

6

Reactant 3

HCID 47654-Hydroxybenzenesulfonic acidHCID 109241-Iodo-3-methylbutaneHCID 14798Sodium Hydroxide

Product 1

HCID 23701366Sodium 4-(3-methylbutoxy)benzenesulfonate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

A solution of 4-hydroxybenzenesulfonic acid (10.0 grams, 43.1 mmole) and sodium hydroxide (3.3 grams, 83 mmole) in water (40 mL) was mixed with a solution of 1-iodo-3-methylbutane (11.3 mL, 86.4 mmole) in isopropanol (60 mL) and the resulting mixture was heated at reflux for 2 days. The isopropanol was removed by evaporation under vacuum. The title compound, 10.0 grams (87%), was collected by filtration and washed with isopropanol.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 2 days
  3. customThe isopropanol was removed by evaporation under vacuum
  4. filtrationThe title compound, 10.0 grams (87%), was collected by filtration
  5. washwashed with isopropanol

Sources & evidence

ORD record
ord-3acf1fc0607243d78b91487c2bf469ac
Source dataset
uspto-grants-2000_07
Patent number
US06087392

Reaction notes

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