1,2-Dichloroethane → HCID 10612804, compound

HRID 1488579Notes

Reaction equation

HRID 1488579 reaction equation
I(Cl)(=O)=O.I(Cl)(=O)=O.C([N+](C)(C)C)C1C=CC=CC=1.[C:20]([C:24]1[C:29]2[O:30][CH2:31][C:32]([CH3:34])([CH3:33])[C:28]=2[CH:27]=[C:26]([C:35](=[O:37])[CH3:36])[CH:25]=1)([CH3:23])([CH3:22])[CH3:21].[Cl:38]CCCl>CO>[C:20]([C:24]1[C:29]2[O:30][CH2:31][C:32]([CH3:34])([CH3:33])[C:28]=2[CH:27]=[C:26]([C:35](=[O:37])[CH2:36][Cl:38])[CH:25]=1)([CH3:23])([CH3:21])[CH3:22]

Participants

5

Reactant 3

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

Product 1

HCID 10612804HCID 10612804, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of benzyltrimethylammonium dichloroiodate (18.18 g, 52.2 mmol), 1-(7-tert-butyl-3,3-dimethyl-2,3-dihydrobenzo[b]furan-5-yl)-ethan-1-one (6.65 g, 27.0 mmol), 325 mL of 1,2-dichloroethane, and 130 mL of methanol is heated at reflux for 1.5 h. The reaction mixture is cooled to room temperature and concentrated in vacuo; 5% aqueous sodium bisulfite solution (126 mL) is added to the residue obtained. This mixture is extracted with ether and the extract is dried over anhydrous magnesium sulfate and concentrated to afford 8.38 g of the title compound as a reddish solid.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 1.5 h
  3. concentrationconcentrated in vacuo
  4. addition5% aqueous sodium bisulfite solution (126 mL) is added to the residue
  5. customobtained
  6. extractionThis mixture is extracted with ether
  7. dry with materialthe extract is dried over anhydrous magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-440c49ed3acb4b8198cf40ccd1e60f84
Source dataset
uspto-grants-1997_10
Patent number
US05674891

Reaction notes

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