Chloroform → 6-Chloro-5-hydroxy-2,2-dimethyl-benzofuran-3-one

HRID 1871846Notes

Reaction equation

HRID 1871846 reaction equation
O[C:2]1[C:10]2[O:9][C:8]([CH3:12])([CH3:11])[C:7](=[O:13])[C:6]=2[CH:5]=[CH:4]C=1.ClN(C(C)C)C(C)C.C(NC(C)C)(C)C.Cl[O-:30].[Na+].[CH:32]([Cl:35])(Cl)Cl>>[Cl:35][C:32]1[C:4]([OH:30])=[CH:5][C:6]2[C:7](=[O:13])[C:8]([CH3:12])([CH3:11])[O:9][C:10]=2[CH:2]=1

Participants

6

Reactant 5

HCID 6212Chloroform2×HCID 7912DiisopropylamineHCID 32745N-Chloro-N,N-diisopropylamineHCID 873033-Ketocarbofuran phenolHCID 23665760Sodium Hypochlorite

Product 1

HCID 186893816-Chloro-5-hydroxy-2,2-dimethyl-benzofuran-3-one

Procedure

25 mmol 7-Hydroxy-2,2-dimethyl-benzofuran-3-one and 30 g silica gel are stirred in 200 ml chloroform. A solution of 25 mmol N-chloro-diisopropylamine in 100 ml chloroform (prepared from diisopropylamine and aqueous sodium hypochlorite solution, extracted in chloroform, concentration determined iodometrically) is added dropwise. After stirring for 10 hours it is filtered and the filtrate is shaken out with water. The solution is dried over sodium sulfate. The solvent is removed by distillation at 300 mbar. The residue is separated by column chromatography (silica gel: ethyl acetate).

Workup

  1. extractionextracted in chloroform
  2. concentrationconcentration determined iodometrically)
  3. additionis added dropwise
  4. filtrationis filtered
  5. stirringthe filtrate is shaken out with water
  6. dry with materialThe solution is dried over sodium sulfate
  7. customThe solvent is removed by distillation at 300 mbar
  8. customThe residue is separated by column chromatography (silica gel: ethyl acetate)

Sources & evidence

ORD record
ord-3716ee726c354d14860f7b291bc859a9
Source dataset
uspto-grants-2000_08
Patent number
US06107036

Reaction notes

Loading…