Potassium Hydroxide → Sodium 4-(6-hydroxyhexyl)oxybenzenesulfonate

HRID 10605Notes

Reaction equation

HRID 10605 reaction equation
[Na+:1].[OH:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([O-:12])(=[O:11])=[O:10])=[CH:5][CH:4]=1.[OH-].[K+].Br[CH:16]([OH:22])[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]>C(O)C>[OH:22][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([O-:12])(=[O:10])=[O:11])=[CH:5][CH:4]=1.[Na+:1]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 4379756Sodium 4-hydroxybenzenesulfonateHCID 21981760Bromohexanol

Product 1

HCID 23717227Sodium 4-(6-hydroxyhexyl)oxybenzenesulfonateYield 98.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Into a three-necked round-bottom flask equipped with a magnetic stirring bar and a reflux condenser were added 4-hydroxybenzenesulfonicacid sodium salt (30.0 grams (g), 0.13 mol), potassium hydroxide (9.0 g, 0.16 mol) and distilled water (60 milliliter (ml)). 1-Bromohexanol (23.16 g, 0.13 mol) dissolved in ethanol (50 ml) was added drop wise into the reaction mixture at room temperature. The reaction mixture was refluxed for 24 hours and then cooled to room temperature. The precipitated product was filtered and washed with chloroform to remove excess of 1-bromohexanol. The product was dried under vacuum at 70° C. for 12 hours to provide 38.06 g of sodium 4-(6-hydroxyhexyl)oxybenzenesulfonate (92% yield).

Workup

  1. customInto a three-necked round-bottom flask equipped with a magnetic stirring bar and a reflux condenser
  2. distillationdistilled water (60 milliliter (ml))
  3. additionwas added drop wise into the reaction mixture at room temperature
  4. temperatureThe reaction mixture was refluxed for 24 hours
  5. filtrationThe precipitated product was filtered
  6. washwashed with chloroform
  7. customto remove excess of 1-bromohexanol
  8. customThe product was dried under vacuum at 70° C. for 12 hours

Sources & evidence

ORD record
ord-62574a4f57594484b87becc8b7f760e8
Source dataset
uspto-grants-2006_08
Patent number
US07094861B2

Reaction notes

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