1,2-Dichloroethane → HCID 69851286, compound

HRID 1602309Notes

Reaction equation

HRID 1602309 reaction equation
I(Cl)(=O)=O.I(Cl)(=O)=[O:6].C([N+](C)(C)C)[C:10]1[CH:15]=CC=CC=1.C(C1[CH:33]=[C:32]([C:34]([CH3:37])([CH3:36])[CH3:35])[C:26]2[O:27][CH2:28][C:29]([CH3:31])([CH3:30])[C:25]=2C=1)(=O)C.Cl[CH2:39][CH2:40][Cl:41]>CO>[Cl:41][C:40]1[CH:33]=[C:32]([C:34]([CH3:35])([CH3:36])[CH3:37])[C:26]2[O:27][CH:28]([C:15](=[O:6])[CH3:10])[C:29]([CH3:30])([CH3:31])[C:25]=2[CH:39]=1

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 10514594HCID 10514594, compoundHCID 56924451Trimethylbenzylammonium Dichloroiodate

Product 1

HCID 69851286HCID 69851286, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of benzyltrimethylammonium dichloroiodate (31.70 g, 91.0 mmol), 5-acetyl-7-tert-butyl-2,3-dihydro-3,3-dimethylbenzo[b]furan (12.35 g, 50.2 mmol), 300 mL of 1,2-dichloroethane, and 120 mL of methanol is heated at reflux for 13 h. The reaction mixture is cooled to room temperature and concentrated in vacuo; 5% aqueous sodium bisulfite solution (125 mL) is added to the residue obtained. This mixture is extracted with ether; the extract is washed with aqueous sodium bicarbonate solution and with brine, dried over anhydrous magnesium sulfate, and concentrated to produce about 14.09 g (100%) of 5-chloro-acetyl-7-tert-butyl-2,3-dihydro-3,3-dimethylbenzo[b]furan as a reddish solid: mp 76-77° C.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 13 h
  3. concentrationconcentrated in vacuo
  4. addition5% aqueous sodium bisulfite solution (125 mL) is added to the residue
  5. customobtained
  6. extractionThis mixture is extracted with ether
  7. washthe extract is washed with aqueous sodium bicarbonate solution and with brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-27902d06651e45f5ab9461fb5a86f694
Source dataset
uspto-grants-1999_11
Patent number
US05981547

Reaction notes

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