Cesium carbonate → HCID 22669607, compound

HRID 1007481Notes

Reaction equation

HRID 1007481 reaction equation
C[C:2]1[C:3]([CH3:10])=[C:4]([CH:6]=[CH:7][C:8]=1[OH:9])[OH:5].[C:11](=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C1COCC1>[OH:5][C:4]1[C:3]([CH3:10])=[CH:2][C:8]([O:9][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[CH:7][C:6]=1[CH3:11]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 11430Potassium CarbonateHCID 691002,3-DimethylhydroquinoneHCID 79177tert-Butyl bromoacetate

Product 1

HCID 22669607HCID 22669607, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

10 g of dimethylhydroquinone are dissolved in 750 ml of a mixture of 40% DMF and 60% THF and treated with 117 g of caesium carbonate. 14.1 g of tert-butyl bromoacetate are added dropwise at −25° C. and the reaction mixture is stirred for 17 hours at room temperature. After addition of 10 g of potassium carbonate the reaction mixture is stirred for 24 hours at room temperature, poured onto water and extracted twice with ethyl acetate. The combined organic phases are washed with NaCl solution, dried over sodium sulphate and the solvent is removed in vacuo. By chromatographic purification (cyclohexane/ethyl acetate) 1.27 g of tert-butyl (4-hydroxy-3,5-dimethylphenoxy)acetate are obtained.

Workup

  1. stirringis stirred for 24 hours at room temperature
  2. additionpoured onto water
  3. extractionextracted twice with ethyl acetate
  4. washThe combined organic phases are washed with NaCl solution
  5. dry with materialdried over sodium sulphate
  6. customthe solvent is removed in vacuo
  7. customBy chromatographic purification (cyclohexane/ethyl acetate) 1.27 g of tert-butyl (4-hydroxy-3,5-dimethylphenoxy)acetate
  8. customare obtained

Sources & evidence

ORD record
ord-674c77ca14184f08af7aca4292817e68
Source dataset
uspto-grants-2004_09
Patent number
US06794406B2

Reaction notes

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