1,2-Dichloroethane → HCID 10612804, compound

HRID 2257258Notes

Reaction equation

HRID 2257258 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-53c570d6ec2745679747aa86cdb11688
Source dataset
uspto-grants-1997_08
Patent number
US05656661

Reaction notes

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