1-Pentanol → 10-Phenyl-10-phenoxathiinium 2,4,6-tricyclohexylbenzoate

HRID 529871Notes

Reaction equation

HRID 529871 reaction equation
[CH:1]1([C:7]2[CH:15]=[C:14]([CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)[CH:13]=[C:12]([CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)[C:8]=2[C:9]([O-:11])=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Na+].COS([O-])(=O)=O.[C:35]1([S+:41]2[C:54]3[CH:53]=[CH:52][CH:51]=[CH:50][C:49]=3[O:48][C:47]3[C:42]2=[CH:43][CH:44]=[CH:45][CH:46]=3)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.C(C(C)=O)(C)C.C(O)CCCC>O>[CH:22]1([C:12]2[CH:13]=[C:14]([CH:16]3[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]3)[CH:15]=[C:7]([CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[C:8]=2[C:9]([O-:11])=[O:10])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.[C:35]1([S+:41]2[C:42]3[CH:43]=[CH:44][CH:45]=[CH:46][C:47]=3[O:48][C:49]3[C:54]2=[CH:53][CH:52]=[CH:51][CH:50]=3)[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

6

Reactant 4

HCID 62761-PentanolHCID 112513-Methyl-2-butanoneHCID 118556698Sodium 2,4,6-tricyclohexylbenzoateHCID 13173563310-Phenyl-10-phenoxathiinium methylsulfate

Product 1

HCID 13173563510-Phenyl-10-phenoxathiinium 2,4,6-tricyclohexylbenzoateYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 100-mL eggplant shaped flask was charged with 1.0 g of sodium 2,4,6-tricyclohexylbenzoate (prepared in Synthesis Example 1-6), 0.9 g of 10-phenyl-10-phenoxathiinium methylsulfate (prepared in Synthesis Example 1-8), 10 g of methyl isopropyl ketone, 10 g of 1-pentanol, and 5 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 30 g of diisopropyl ether. The crystal precipitate was filtered and dried, obtaining the target compound, 10-phenyl-10-phenoxathiinium 2,4,6-tricyclohexylbenzoate as white crystal. Amount 1.4 g, yield 88%.

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 30 g of diisopropyl ether
  8. filtrationThe crystal precipitate was filtered
  9. customdried

Sources & evidence

ORD record
ord-add922ec881c40459978d43aa6161523
Source dataset
uspto-grants-2016_05
Patent number
US09348227B2

Reaction notes

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