Hydrochloric Acid → Ethyl 3-hydroxy-3-methyloctanoate

HRID 1172155Notes

Reaction equation

HRID 1172155 reaction equation
[CH3:1][C:2](=[O:8])[CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].Br[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12].II.Cl>O1CCOCC1.[Zn]>[OH:8][C:2]([CH3:1])([CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 807IodineHCID 7748Ethyl bromoacetateHCID 80512-Heptanone

Product 1

HCID 3020787Ethyl 3-hydroxy-3-methyloctanoate

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-heptanone (10.1 mL) in 1,4-dioxane (150 mL) were added ethyl bromoacetate (9.6 mL), zinc (8.5 g) and iodine (3.7 g) at room temperature and the solution was sonicated. After 2 hours 1N hydrochloric acid was added dropwise to the reaction solution, which was extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate and concentrated. The obtained residue purified by flush column chromatography (n-hexane:ethyl acetate=15:1), to give the title compound (13.9 g) having the following physical data.

Workup

  1. customthe solution was sonicated
  2. extractionwas extracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe obtained residue purified
  7. customby flush column chromatography (n-hexane:ethyl acetate=15:1)

Sources & evidence

ORD record
ord-3a07a12d160241b7be7df4c944b3ec71
Source dataset
uspto-grants-2010_11
Patent number
US07833995B2

Reaction notes

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