1-Pentanol → Triphenylsulfonium 2,4,6-triisopropylbenzoate

HRID 529865Notes

Reaction equation

HRID 529865 reaction equation
[CH:1]([C:4]1[CH:12]=[C:11]([CH:13]([CH3:15])[CH3:14])[CH:10]=[C:9]([CH:16]([CH3:18])[CH3:17])[C:5]=1[C:6]([O-:8])=[O:7])([CH3:3])[CH3:2].[Na+].COS([O-])(=O)=O.[C:26]1([S+:32]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(C(C)=O)(C)C.C(O)CCCC>O>[CH:1]([C:4]1[CH:12]=[C:11]([CH:13]([CH3:15])[CH3:14])[CH:10]=[C:9]([CH:16]([CH3:18])[CH3:17])[C:5]=1[C:6]([O-:8])=[O:7])([CH3:3])[CH3:2].[C:39]1([S+:32]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1

Participants

6

Reactant 4

HCID 62761-PentanolHCID 112513-Methyl-2-butanoneHCID 22995011Triphenylsulfonium methylsulfateHCID 118556701Sodium 2,4,6-triisopropylbenzoate

Product 1

HCID 131735631Triphenylsulfonium 2,4,6-triisopropylbenzoateYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 1-L eggplant shaped flask was charged with 22.4 g of sodium 2,4,6-triisopropylbenzoate (prepared in Synthesis Example 1-2), 31.1 g of triphenylsulfonium methylsulfate, 90 g of methyl isopropyl ketone, 90 g of 1-pentanol, and 40 g of water, which were stirred at room temperature for 1 hour. The organic layer was separated from the reaction mixture and washed with water. After washing, the organic layer was concentrated by distilling off the solvent. The liquid concentrate was crystallized from 300 g of diisopropyl ether. The crystal precipitate was filtered and dried, obtaining the target compound, triphenylsulfonium 2,4,6-triisopropylbenzoate as white crystal. Amount 40.4 g, yield 80%.

Workup

  1. customThe organic layer was separated from the reaction mixture
  2. washwashed with water
  3. washAfter washing
  4. concentrationthe organic layer was concentrated
  5. distillationby distilling off the solvent
  6. concentrationThe liquid concentrate
  7. customwas crystallized from 300 g of diisopropyl ether
  8. filtrationThe crystal precipitate was filtered
  9. customdried

Sources & evidence

ORD record
ord-c896c67c342f48fa8f84747cf3535aa3
Source dataset
uspto-grants-2016_05
Patent number
US09348227B2

Reaction notes

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