Potassium Carbonate → 2-[2-(3-Tert-butyl-phenoxy)-ethyl]-[1,3]dioxane

HRID 1158783

Reaction equation

HRID 1158783 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([OH:11])[CH:8]=[CH:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].Br[CH2:13][CH2:14][CH:15]1[O:20][CH2:19][CH2:18][CH2:17][O:16]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:1]([C:5]1[CH:6]=[C:7]([CH:8]=[CH:9][CH:10]=1)[O:11][CH2:13][CH2:14][CH:15]1[O:20][CH2:19][CH2:18][CH2:17][O:16]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11450Phenol, 3-(1,1-dimethylethyl)-HCID 5206561,3-Dioxane, 2-(2-bromoethyl)-

Product 1

HCID 595485522-[2-(3-Tert-butyl-phenoxy)-ethyl]-[1,3]dioxaneYield 112.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-tert-butyl-phenol (1.50 g, 10 mmol), 2-(2-bromo-ethyl)-[1,3]dioxane (1.38 g, 10 mmol) and potassium carbonate (2.15 g, 11 mmol) in 20 ml acetonitrile was heated to reflux for 16 hours. After cooling, the solvent was removed under reduced pressure and the residue partitioned between diethyl ether and water. The isolated organic layer was washed with water, dried with magnesium sulfate, filtered and the solvent removed under reduced pressure to give 2.97 g of crude 2-[2-(3-tert-butyl-phenoxy)-ethyl]-[1,3]dioxane, which was used without further purification.

Workup

  1. temperatureto reflux for 16 hours
  2. temperatureAfter cooling
  3. customthe solvent was removed under reduced pressure
  4. customthe residue partitioned between diethyl ether and water
  5. washThe isolated organic layer was washed with water
  6. dry with materialdried with magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-e8f123f0f43c459098a2e50796ba7a4a
Source dataset
uspto-grants-2010_10
Patent number
US07812019B2

Linked notes

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