Potassium Carbonate → 7-(2,6-Dichloro-4-nitrophenoxy)-2,2-dimethyl-2,3-dihydro-1-benzofuran

HRID 978478Notes

Reaction equation

HRID 978478 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([Cl:11])[C:3]=1Cl.[CH3:13][C:14]1([CH3:24])[CH2:18][C:17]2[CH:19]=[CH:20][CH:21]=[C:22]([OH:23])[C:16]=2[O:15]1.C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[Cl:11][C:4]1[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=[C:2]([Cl:1])[C:3]=1[O:23][C:22]1[C:16]2[O:15][C:14]([CH3:24])([CH3:13])[CH2:18][C:17]=2[CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 152782,3-Dihydro-2,2-dimethyl-7-benzofuranolHCID 883653,4,5-Trichloronitrobenzene

Product 1

HCID 132459927-(2,6-Dichloro-4-nitrophenoxy)-2,2-dimethyl-2,3-dihydro-1-benzofuran

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

To a solution containing 32.83 g of 1,2,3-trichloro-5-nitrobenzene and 26.11 g of 2,3-dihydro-2,2-dimethyl-7-hydroxybenzofuran in 300 ml of methyl ethyl ketone under an atmosphere of nitrogen and at room temperature was added 21.98 g of anhydrous potassium carbonate. The reaction mixture was heated to reflux. Reflux was maintained for 30 hrs. The reaction mixture was cooled to room temperature and the solvents removed. The tan solid residue was dissolved in hot hexane containing a little ethyl acetate. This was filtered and the filtrate allowed to cool to room temperature then placed in freezer to cool further to promote crystallization. The crystals were collected and placed in a vacuum dessicator for drying. A second crop of crystals was obtained from the mother liquors. This afforded 29.2 g of pale tan crystals. mp 105°-110° C. NMR (CDCl3): 1.47 (s, 6H), 3.03 (s, 2H), 6.3-7.0 (m, 3H), 8.22 (s, 2H).

Workup

  1. temperatureThe reaction mixture was heated to reflux
  2. temperatureReflux
  3. temperaturewas maintained for 30 hrs
  4. customthe solvents removed
  5. dissolutionThe tan solid residue was dissolved in hot hexane containing a little ethyl acetate
  6. filtrationThis was filtered
  7. temperatureto cool to room temperature
  8. temperatureto cool further
  9. customcrystallization
  10. customThe crystals were collected
  11. customfor drying
  12. customA second crop of crystals was obtained from the mother liquors

Sources & evidence

ORD record
ord-831d3a3a59bc4e58b167a379a86625ab
Source dataset
uspto-grants-1987_05
Patent number
US04665097

Reaction notes

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