Acetone → HCID 12493710, compound

HRID 905288Notes

Reaction equation

HRID 905288 reaction equation
C1(C2CCCCCC=2)C[CH2:6][CH2:5][CH2:4][C:3](=[O:8])C=1.[Br:16]N1C(C)(C)C(=O)N(Br)C1=O.[CH3:27][C:28]([CH3:30])=[O:29]>O>[Br:16][CH:30]1[CH:28]([OH:29])[CH2:27][CH:4]2[CH:5]1[CH2:6][C:3]2=[O:8]

Participants

5

Reactant 3

HCID 180AcetoneHCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 66641332HCID 66641332, compound

Product 1

HCID 12493710HCID 12493710, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 1 g of bicycloheptenone (III) dissolved in the mixture of 20 ml of acetone and 5 ml of water, 1.5 g of 1,3-dibromo-5,5-dimethyl-hydantoin was added in portions under constant stirring. After 16 hours at room temperature the solvent was evaporated under reduced pressure. The residue was dissolved in 10 ml of water and extracted several times with dichloromethane. Obtained organic extracts were washed with brine, dried over magnesium sulfate and evaporated. A residuum in the form of a yellow oil was then separated by silica-gel column chromatography with solvent mixture of 20% ethyl acetate in light petroleum to obtain 2-bromo-3-hydroxybicyclo[3.2.0]heptan-6-one] (IV) (U.S. Pat. No. 4,272,629).

Workup

  1. additionwas added in portions under constant stirring
  2. customAfter 16 hours at room temperature the solvent was evaporated under reduced pressure
  3. dissolutionThe residue was dissolved in 10 ml of water
  4. extractionextracted several times with dichloromethane
  5. washObtained organic extracts were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. customA residuum in the form of a yellow oil was then separated by silica-gel column chromatography with solvent mixture of 20% ethyl acetate in light petroleum

Sources & evidence

ORD record
ord-69a4a7e3c999415ea4b6e011e9252bfa
Source dataset
uspto-grants-1983_12
Patent number
US04423068

Reaction notes

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