Acetic Anhydride → HCID 13401939, compound

HRID 424337Notes

Reaction equation

HRID 424337 reaction equation
[C:1]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:6]=[CH:5][C:4](CC([O-])=O)=[CH:3][CH:2]=1.[Na+].F[B-](F)(F)F.[C:23]1([C:29]2[CH:34]=[C:33]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH:32]=[C:31]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[O+]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[C:47](OC(=O)C)(=O)C>>[C:23]1([C:29]2[CH:47]=[C:31]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[CH:32]=[C:33]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:34]=2[C:14]2[CH:15]=[CH:16][C:11]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[CH:12][CH:13]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 9930615Pyrylium, 2,4,6-triphenyl-, tetrafluoroborate(1-)HCID 23710942HCID 23710942, compound

Product 1

HCID 13401939HCID 13401939, compound

Procedure

Sodium 4-biphenylacetate (25.0 g, 0.106 mol.) was placed in a suspension of 2,4,6-triphenylpyrylium tetrafluoroborate (41.0 g, 0.106 mol.) in 80 mL of acetic anhydride under nitrogen atmosphere and refluxed for 24 hours. The crude product was extracted with a 7:3 ratio mixture of hexane/dichloromethane. The solvent was stripped, and the crude product sublimed 4 times to achieve 99% purity. The practical yield following sublimations was 20%.

Workup

  1. temperaturerefluxed for 24 hours
  2. extractionThe crude product was extracted with a 7:3 ratio mixture of hexane/dichloromethane
  3. customThe practical yield

Sources & evidence

ORD record
ord-1dcf436f66534a10971573fec8993d93
Source dataset
uspto-grants-2012_01
Patent number
US08105700B2

Reaction notes

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