Iodine → (1-Hydroxy-cyclohexyl)-acetic acid ethyl ester

HRID 550281

Reaction equation

HRID 550281 reaction equation
[C:1]1(=[O:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.II.Br[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].S(=O)(=O)(O)O>C1COCC1.[Zn]>[CH2:15]([O:14][C:12](=[O:13])[CH2:11][C:1]1([OH:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[CH3:16]

Participants

7

Reactant 4

HCID 807IodineHCID 1118Sulfuric AcidHCID 7748Ethyl bromoacetateHCID 7967Cyclohexanone

Product 1

HCID 219250(1-Hydroxy-cyclohexyl)-acetic acid ethyl esterYield 95.2%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of cyclohexanone (9.52 g, 97.0 mmol), a zinc powder (7.6 g, 116.4 mmol) and a small amount of iodine in THF (100 ml) was added dropwise ethyl bromoacetate (11.8 ml, 106.7 mmol) under a nitrogen atmosphere, and the mixture was heated under reflux for 5 hrs. 10% Sulfuric acid (100 ml) was carefully added under ice-cooling, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous MgSO4, and concentrated under reduced pressure to give the title compound (17.2 g, 94%) as a colorless oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 5 hrs
  3. temperaturecooling
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution
  6. dry with materialdried over anhydrous MgSO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d2e026c0189145f6877d14a4e2913dec
Source dataset
uspto-grants-2011_05
Patent number
US07943770B2

Linked notes

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