Water → HCID 70266525, compound

HRID 1858512Notes

Reaction equation

HRID 1858512 reaction equation
CC[O:3][C:4]([CH2:6][CH:7]1[C:12](=[O:13])[CH2:11][CH2:10][CH2:9][CH2:8]1)=[O:5].[Br:14]Br.O.C(OCC)(=O)C>C(COC)OC>[C:4]([OH:5])(=[O:3])[CH3:6].[CH2:6]([CH:7]1[C:12](=[O:13])[CH2:11][CH2:10][CH2:9][CH:8]1[Br:14])[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 24408BromineHCID 91229Ethyl 2-oxocyclohexylacetate

Product 1

HCID 70266525HCID 70266525, compoundYield 35.9%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of ethyl 2-cyclohexanone acetate (1.0 g) in dimethoxyethane (15 ml) was added bromine (911 mg) at ice-cooling. After stirring at room temperature for 1 hour, the solution was poured into a mixture of water and ethyl acetate. The separated organic layer was washed with aqueous sodium hydrogen sulfite, sodium hydrogen carbonate and saturated sodium chloride orderly, and dried over magnesium sulfate and evaporated under reduced pressure. The residue was subjected to column chromatography on silica gel (eluent: ethyl acetate/n-hexane) to give ethyl 2-bromo-6-cyclohexanone acetate (258 mg).

Workup

  1. temperaturecooling
  2. washThe separated organic layer was washed with aqueous sodium hydrogen sulfite, sodium hydrogen carbonate and saturated sodium chloride orderly
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-7ac440b370a84b5a843eda8e9953a873
Source dataset
uspto-grants-2000_11
Patent number
US06150351

Reaction notes

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