Acetic Anhydride → HCID 131726830, compound

HRID 900518Notes

Reaction equation

HRID 900518 reaction equation
[S:1]([C:5]([C:8]([C:11]([C:14]([F:17])([F:16])[F:15])([F:13])[F:12])([F:10])[F:9])([F:7])[F:6])([O-:4])(=[O:3])=[O:2].[OH:18][C:19]1[C:24]([CH3:25])=[CH:23][C:22]([S+:26]([CH3:28])[CH3:27])=[CH:21][C:20]=1[CH3:29].C(=O)([O-])[O-].[K+].[K+].[C:36](OC(=O)C)(=[O:38])[CH3:37]>CC(C)=O>[S:1]([C:5]([C:8]([C:11]([C:14]([F:15])([F:16])[F:17])([F:12])[F:13])([F:10])[F:9])([F:7])[F:6])([O-:4])(=[O:3])=[O:2].[C:36]([O:18][C:19]1[C:20]([CH3:29])=[CH:21][C:22]([S+:26]([CH3:27])[CH3:28])=[CH:23][C:24]=1[CH3:25])(=[O:38])[CH3:37]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 11430Potassium CarbonateHCID 22023911HCID 22023911, compound

Product 1

HCID 131726830HCID 131726830, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

20.0 g of 4-Hydroxy-3,5-dimethyl phenyl dimethyl sulphonium nonaflate was taken in a round bottom flask, 50 ml acetone and 5.73 g of potassium carbonate were added and then 4.23 g of acetic anhydride was added dropwise at room temperature. The resulting mixture was stirred for 4 hours. The solution was then extracted with chloroform, washed with water, dried over sodium sulphate and filtered. The solution was concentrated and drowned into ether; a precipitate was formed, filtered and dried in the vacuum dryer at less than 40° C., yielding 4-acetoxy-3,5-dimethyl phenyl dimethyl sulphonium nonaflate, 15.0 g (70%). The solid product gave the following analytical results: 1H NMR (DMSO-d6), 2.35 (s, 6H, 2CH3); 2.45 (s, 3h, CH3); 3.5 (s, 6H, 2CH3); 7.80 (s, 2H, aromatic), mp 168° C.

Workup

  1. extractionThe solution was then extracted with chloroform
  2. washwashed with water
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. concentrationThe solution was concentrated
  6. customa precipitate was formed
  7. filtrationfiltered
  8. customdried in the vacuum dryer at less than 40° C.

Sources & evidence

ORD record
ord-37e71e6123f648bbb8a2b5e6a107820e
Source dataset
uspto-grants-2008_04
Patent number
US07358408B2

Reaction notes

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