Water → Ethyl acetate hexane

HRID 2219223Notes

Reaction equation

HRID 2219223 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Br[CH2:11][CH2:12]Br.[OH2:14]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1>[CH3:5][CH2:6][CH2:1][CH2:2][CH2:3][CH3:4].[CH3:11][CH2:12][O:14][C:1]([CH3:6])=[O:7]

Participants

7

Reactant 4

HCID 962WaterHCID 996PhenolHCID 78391,2-DibromoethaneHCID 24758Sodium hydride

Product 1

HCID 21226206Ethyl acetate hexaneYield 16%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the corresponding phenol (12.9 mmol) and tetrabutylammonium iodide (478 mg, 1.29 mmol) in THF (25 mL) at room temperature, NaH (60% in oil, 0.77 g, 19.4 mmol) was slowly added. The mixture was stirred for 30 minutes, and then 1,2-dibromoethane (3.36 mL, 38.8 mmol) was added. The mixture was stirred at room temperature under argon overnight. Water was added (50 mL) and the mixture was extracted with EtOAc (2×50 mL). The organic layer was dried over MgSO4 and concentrated. The crude product 8a, 8b was purified by chromatography in silica gel, eluent hexane/EtOAc 6:1 (16-25% yield).

Workup

  1. stirringThe mixture was stirred at room temperature under argon overnight
  2. extractionthe mixture was extracted with EtOAc (2×50 mL)
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated
  5. customThe crude product 8a, 8b was purified by chromatography in silica gel

Sources & evidence

ORD record
ord-ae5c0a470d34444bb5385199beaa5abd
Source dataset
uspto-grants-2008_08
Patent number
US07414063B2

Reaction notes

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