Propargyl bromide → 2-Propynyloxyxanthen-9-one

HRID 396413Notes

Reaction equation

HRID 396413 reaction equation
[OH:1][C:2]1[CH:15]=[CH:14][C:13]2[O:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[O:16])[C:4]=2[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:23](Br)[C:24]#[CH:25]>CC(C)=O>[C:23]([O:1][C:2]1[CH:15]=[CH:14][C:13]2[O:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[O:16])[C:4]=2[CH:3]=1)#[C:24][CH3:25]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 747082-Hydroxyxanthone

Product 1

HCID 699700042-Propynyloxyxanthen-9-one

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2-hydroxyxanthen-9-one (2.12 g, 0.01 mol), K2CO3 (2.8 g, 0.02 mol), Kl (0.166 g, 0.001 mol), propargyl bromide (1.78 g, 0.015 mol) and acetone (100 mL) was refluxed 10 h and hot filtered. The solvent was evaporated and the residue was crystallized by toluene. This yields 2.25 g of a product with the following characteristics: m.p.153-154° C.; 1H NMR (CDCl3) δ: 2.58 (m, 1H), 4.8 (s, 2H), 7.35-8.38 (m, 7H).

Workup

  1. temperaturewas refluxed 10 h
  2. customThe solvent was evaporated
  3. customthe residue was crystallized by toluene

Sources & evidence

ORD record
ord-d2592acf4fb04b139640e7b2d0fe68bd
Source dataset
uspto-grants-2003_08
Patent number
US06608089B2

Reaction notes

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