Trifluoroacetic acid → 2,2-dimethyl-4-oxo-4H-1,3-benzodioxine-6-carbonitrile

HRID 733508Notes

Reaction equation

HRID 733508 reaction equation
[C:1]([C:3]1[CH:11]=[C:7]([C:8]([OH:10])=[O:9])[C:6]([OH:12])=[CH:5][CH:4]=1)#[N:2].[C:13](O)([C:15](F)(F)F)=O.[C:20](OC(C(F)(F)F)=O)(C(F)(F)F)=O>CC(C)=O>[CH3:20][C:13]1([CH3:15])[O:12][C:6]2[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:11][C:7]=2[C:8](=[O:10])[O:9]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 9845Trifluoroacetic anhydrideHCID 130269355-Cyano-2-hydroxybenzoic acid

Product 1

HCID 597024522,2-dimethyl-4-oxo-4H-1,3-benzodioxine-6-carbonitrileYield 18.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a suspension of 5-cyano salicylic acid (60 g, 0.368 mol) in TFA (134 mL, 1.76 mol) and TFAA (45 mL, 0.32 mol) was added dry acetone (20 mL) and heated to reflux. After each 1 h interval was added 15 mL of dry acetone for 4 times and the reflux continued for 20 h. The reaction mixture was concentrated under vacuum and crude purified by flash column chromatography over silica gel (230-400 mesh) using CH2Cl2 as an eluent to give the title compound as a white solid (12 g, 15%). TLC: CH2Cl2 (100%), Rf: 0.5

Workup

  1. temperatureheated to reflux
  2. concentrationThe reaction mixture was concentrated under vacuum and crude
  3. custompurified by flash column chromatography over silica gel (230-400 mesh)

Sources & evidence

ORD record
ord-973070df46954464aed7fea6f1334c64
Source dataset
uspto-grants-2009_09
Patent number
US07589232B2

Reaction notes

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