Water → Sodium p-benzyloxybenzenesulfonate

HRID 643986Notes

Reaction equation

HRID 643986 reaction equation
[OH-].[Na+:2].O.O.[Na+].[OH:6][C:7]1[CH:12]=[CH:11][C:10]([S:13]([O-:16])(=[O:15])=[O:14])=[CH:9][CH:8]=1.O.[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(O)C>[Na+:2].[CH2:18]([O:6][C:7]1[CH:12]=[CH:11][C:10]([S:13]([O-:16])(=[O:14])=[O:15])=[CH:9][CH:8]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 23666329Sodium P-phenolsulfonate dihydrate

Product 1

HCID 23685655Sodium p-benzyloxybenzenesulfonate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Aqueous NaOH (40 mL of a 15% aqueous solution, 150 mmol) is added to 20 g (86.2 mmol) of 4-hydroxybenzenesulfonic acid sodium salt dihydrate at RT. An additional 20 mL of water is added, and the mixture is warmed slightly to dissolve the salt. Benzyl bromide (19.2 g, 112.1 mmol) in 8 mL of ethanol is then added in several portions. The mixture is heated to reflux. After 30 min, additional 20 mL of water is added, and heating is continued for 3.5 h, followed by continued stirring at RT overnight. After cooling in the refrigerator for 3 h, the solid product is collected by filtration and washed with water (20 mL), ethanol (40 mL), and ether (40 mL) and then dried overnight under vacuum to give 4-benzyloxybenzenesulfonic acid sodium salt.

Workup

  1. temperaturethe mixture is warmed slightly
  2. dissolutionto dissolve the salt
  3. temperatureThe mixture is heated to reflux
  4. temperatureheating
  5. waitis continued for 3.5 h
  6. temperatureAfter cooling in the refrigerator for 3 h
  7. filtrationthe solid product is collected by filtration
  8. washwashed with water (20 mL), ethanol (40 mL), and ether (40 mL)
  9. customdried overnight under vacuum

Sources & evidence

ORD record
ord-4b52d9ded8864a6e8d5ddd66214fd7d5
Source dataset
uspto-grants-2010_04
Patent number
US07700637B2

Reaction notes

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