Ethanol → Sodium 1,3,5-tricyclohexylbenzenesulfonate

HRID 2035325Notes

Reaction equation

HRID 2035325 reaction equation
[CH:1]1([C:7]2[C:8](C3CCCCC3)=[C:9]([CH:13]3[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]3)[CH:10]=[CH:11][CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[S:26]([OH:29])(=[O:28])=[O:27].[OH-].[Na+:31].[CH2:32](O)[CH3:33]>C(Cl)Cl>[CH:13]1([C:9]2([S:26]([O-:29])(=[O:28])=[O:27])[CH:8]=[C:7]([CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[CH:12]=[C:11]([CH:33]3[CH2:32][CH2:3][CH2:2][CH2:1][CH2:6]3)[CH2:10]2)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1.[Na+:31]

Participants

6

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 24638Chlorosulfonic acidHCID 3015433Tricyclohexylbenzene

Product 1

HCID 86655172Sodium 1,3,5-tricyclohexylbenzenesulfonateYield 151.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
3 °C

Procedure

Tricyclohexylbenzene (30 g) was dissolved in 50 ml of methylene chloride, followed by stirring under cooling at 3° C., and 15.2 g of chlorosulfonic acid was slowly added dropwise thereto. After the dropwise addition, the resultant was stirred at room temperature for 5 hours, and 10 g of ice was added thereto. Subsequently, 40 g of 50% aqueous sodium hydroxide solution was added thereto, and 20 g of ethanol was further added thereto. The resultant was stirred at 50° C. for an hour, the insoluble fraction was then removed by filtering, and the resultant was removed by distillation under reduced pressure at 40° C. The precipitated crystals were collected through filtering and washed with hexane, thereby obtaining 30 g of sodium 1,3,5-tricyclohexylbenzene sulfonate.

Workup

  1. additionAfter the dropwise addition
  2. stirringthe resultant was stirred at room temperature for 5 hours
  3. stirringThe resultant was stirred at 50° C. for an hour
  4. customthe insoluble fraction was then removed
  5. filtrationby filtering
  6. customthe resultant was removed by distillation under reduced pressure at 40° C
  7. customThe precipitated crystals were collected
  8. filtrationthrough filtering
  9. washwashed with hexane

Sources & evidence

ORD record
ord-b800b823e37644b090d24a3e166623ea
Source dataset
uspto-grants-2013_11
Patent number
US08574814B2

Reaction notes

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