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

HRID 529869
Notes
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Reaction equation

HRID 529869 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]([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[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:48]1([S+:41]([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 62761-PentanolHCID 112513-Methyl-2-butanoneHCID 22995011Triphenylsulfonium methylsulfateHCID 118556698Sodium 2,4,6-tricyclohexylbenzoate

Product 1

HCID 131735632Triphenylsulfonium 2,4,6-tricyclohexylbenzoateYield 76%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

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 triphenylsulfonium methylsulfate, 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, triphenylsulfonium 2,4,6-tricyclohexylbenzoate as white crystal. Amount 1.2 g, yield 76%.

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-aa88c1169a784c8a95e79d877468e735
Source dataset
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09348227B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes