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

HRID 902767Notes

Reaction equation

HRID 902767 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(OC(C(F)(F)F)=O)(C(F)(F)F)=O.[CH3:26][C:27]([CH3:29])=O>>[CH3:26][C:27]1([CH3:29])[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

4

Reactant 3

HCID 180Acetone2×HCID 9845Trifluoroacetic anhydrideHCID 130269355-Cyano-2-hydroxybenzoic acid

Product 1

HCID 597024522,2-dimethyl-4-oxo-4H-1,3-benzodioxine-6-carbonitrileYield 15%

Procedure

To a suspension of 5-cyano salicylic acid (60 g, 0.368 mol) in TEA (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-3373f06d6e1e43daac4605bad0b0ee54
Source dataset
uspto-grants-2008_04
Patent number
US07365225B2

Reaction notes

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