4-Hydroxybenzenesulfonic acid → Sodium 4-(4-fluorobenzyloxy)benzenesulfonate

HRID 2288117Notes

Reaction equation

HRID 2288117 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.[F:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17]Br)=[CH:15][CH:14]=1.[OH-].[Na+:22]>C(O)C>[F:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][O:1][C:2]2[CH:7]=[CH:6][C:5]([S:8]([O-:11])(=[O:9])=[O:10])=[CH:4][CH:3]=2)=[CH:15][CH:14]=1.[Na+:22]

Participants

5

Reactant 3

HCID 47654-Hydroxybenzenesulfonic acidHCID 14798Sodium HydroxideHCID 680214-Fluorobenzyl bromide

Product 1

HCID 23701365Sodium 4-(4-fluorobenzyloxy)benzenesulfonate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-hydroxybenzenesulfonic acid (5.13 grams, 22.1 mmole) in 1N aqueous sodium hydroxide solution (23 mL) was added a solution of 4-fluorobenzylbromide (3.3 mL, 26.5 mmole) in ethanol (20 mL). The resulting mixture was heated at reflux for 2 days. Upon cooling and standing, a white solid precipitated. The precipitated product, sodium 4-(4-fluorobenzyloxy)benzenesulfonate, 4.95 grams (74%) was collected by filtration and washed with ethyl acetate and diethyl ether.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 2 days
  3. temperatureUpon cooling
  4. customa white solid precipitated
  5. filtrationThe precipitated product, sodium 4-(4-fluorobenzyloxy)benzenesulfonate, 4.95 grams (74%) was collected by filtration
  6. washwashed with ethyl acetate and diethyl ether

Sources & evidence

ORD record
ord-9693202ba0ec44ed9cfbd859074ae69c
Source dataset
uspto-grants-2000_07
Patent number
US06087392

Reaction notes

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