2,6-Dichlorophenol → HCID 11089017, compound

HRID 864658Notes

Reaction equation

HRID 864658 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[O:5][C:4](=[O:14])[CH:3]=1.[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[C:17]=1[OH:23].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[C:17]=1[O:23][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[O:5][C:4](=[O:14])[CH:3]=1

Participants

5

Reactant 3

HCID 68992,6-DichlorophenolHCID 11430Potassium CarbonateHCID 110850882H-1-Benzopyran-2-one, 4-chloro-6-methoxy-

Product 1

HCID 11089017HCID 11089017, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A stirred mixture of 4-chloro-6-methoxycoumarin (1.0 g, 4.75 mmole) , 2,6-dichlorophenol (0.85 g, 5.22 mmole) and K2CO3 (0.98 g, 7.12 mmole) in acetonitrile, under N2, is heated at reflux temperature for 16 hours, cooled to room temperature and poured into ice water. This mixture is extracted several times with ether. The extracts are combined and concentrated in vacuo to give a tan solid residue. The residue is crystallized from ethyl acetate/hexane to afford the title product as tan crystals, 1.17 g (73% yield), mp 170°-171° C., identified by IR, 1HNMR, 13CNMR, and mass spectral analyses.

Workup

  1. temperatureunder N2, is heated
  2. temperatureat reflux temperature for 16 hours
  3. extractionThis mixture is extracted several times with ether
  4. concentrationconcentrated in vacuo
  5. customto give a tan solid residue
  6. customThe residue is crystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-b49a1d195cfb45b3bac4ca3761d2cc05
Source dataset
uspto-grants-1996_10
Patent number
US05563280

Reaction notes

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