Sulfuric Acid → Ethyl 4-bromo-3-oxocyclohexanecarboxylate

HRID 1593613Notes

Reaction equation

HRID 1593613 reaction equation
[Br:1][CH:2]1[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH:3]1[OH:13].OS(O)(=O)=O.C(O)(C)C>CC(C)=O.O>[Br:1][CH:2]1[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][C:3]1=[O:13]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 3776IsopropanolHCID 58999614HCID 58999614, compound

Product 1

HCID 12917736Ethyl 4-bromo-3-oxocyclohexanecarboxylate

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a solution of ethyl 4-bromo-3-hydroxycyclohexanecarboxylate (15.06 g) in acetone (300 mL) at 0° C. was added CrO3 (12.0 g, 120 mmol), and 2 N H2SO4 (60 mL). The mixture was stirred at room temperature for 30 min. Isopropanol (15 mL) was added and the reaction was stirred for 20 min. The volume was reduced under vacuum then diluted with water and extracted with ethyl acetate. The organic layer was washed with water, then brine, was dried over MgSO4 and concentrated in vacuo. Purification by chromatography on silica gel (10% EtOAc in hexane) afforded 6.7 g of tide compound.

Workup

  1. stirringthe reaction was stirred for 20 min
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialbrine, was dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customPurification by chromatography on silica gel (10% EtOAc in hexane)
  7. customafforded 6.7 g of tide compound

Sources & evidence

ORD record
ord-1aa439f5d3704070b1ba649c12a848de
Source dataset
uspto-grants-2007_11
Patent number
US07297704B2

Reaction notes

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