Propylene Oxide → HCID 21274895, compound

HRID 1382528Notes

Reaction equation

HRID 1382528 reaction equation
C1OC1C.[I-].[CH3:6][S+:7]([CH3:9])[CH3:8].[Cl:10][C:11]1[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=[CH:26][C:12]=1[O:13][C:14]1[CH:15]=[CH:16][C:17]([N+:23]([O-:25])=[O:24])=[C:18]([CH:22]=1)[C:19]([OH:21])=[O:20]>O1CCCC1>[Cl:10][C:11]1[CH:29]=[C:28]([C:30]([F:31])([F:32])[F:33])[CH:27]=[CH:26][C:12]=1[O:13][C:14]1[CH:15]=[CH:16][C:17]([N+:23]([O-:25])=[O:24])=[C:18]([CH:22]=1)[C:19]([O-:21])=[O:20].[CH3:6][S+:7]([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 6378Propylene OxideHCID 44073AcifluorfenHCID 75127Trimethylsulfonium iodide

Product 1

HCID 21274895HCID 21274895, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Trimethyl sulfonium 5-(2-chloro-4-trifluoro-methylphenoxy)-2-nitrobenzoate was prepared by adding an excess of propylene oxide to a solution of trimethyl sulfonium iodide and one equivalent of 5-(2-chloro-4-trifluoromethylphenoxy)-2-nitro benzoic acid in aqueous tetrahydrofuran at 35° C. After 2 hours, the volatile organic compounds were removed under reduced pressure. The remaining aqueous phase was shaken with ether, separated and the water was then removed under reduced pressure to yield trimethyl sulfonium 5-(2-chloro-4-trifluoromethylphenoxy)-2-nitrobenzoate. It was also prepared by regenerating Amberlite 200 cation exchange resin with about 10 equivalents of trimethylsulfonium iodide (Amberlite 200 is a macroreticular, high capacity, strongly acidic cation exchange resin having sulfonic acid functionality, prepared from a styrene divinylbenzene copolymer). Thereafter the column containing the regenerated resin was washed with deionized water and a solution of sodium-5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate was then passed down the column to yield trimethylsulfonium 5-(2-chloro-4-trifluoromethyl-phenoxy)-2-nitrobenzoate.

Workup

  1. customthe volatile organic compounds were removed under reduced pressure
  2. customseparated
  3. customthe water was then removed under reduced pressure

Sources & evidence

ORD record
ord-65089deb54f04350a283f434f19eb48e
Source dataset
uspto-grants-1989_02
Patent number
US04806682

Reaction notes

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