Diethyl Ether → HCID 57166946, compound

HRID 986739Notes

Reaction equation

HRID 986739 reaction equation
[CH2:1]([OH:3])[CH3:2].[CH3:4][C:5]1[CH:14]=[CH:13][C:8](OC(O)C)=[CH:7][CH:6]=1.[CH2:15]([O:17][CH2:18][CH3:19])C.[OH-].[Na+].S([O:27][CH3:28])(OC)(=O)=O>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH3:4][C:5]1[CH:14]=[CH:13][C:8]([CH:2]([O:27][CH3:28])[CH2:1][O:3][CH2:19][CH:18]([O:17][CH3:15])[C:8]2[CH:7]=[CH:6][C:5]([CH3:4])=[CH:14][CH:13]=2)=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 70444771HCID 70444771, compound

Product 1

HCID 57166946HCID 57166946, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 962WaterSolvent

Procedure

For this reaction, 50 gms. (0.33 mole) of 4-methylphenoxyethanol ethanol and 2.43 gms. (0.0066 mole, 2 mole %) of tetrabutylammonium iodide (TBAI) are charged with 100 mls diethylether (DEE) to a 500 ml. flask fitted with mechanical stirrer, condenser, addition funnel and N2 inlet. Sixty-six gms. (1.65 moles) of sodium hydroxide (as a 50% aqueous solution) are then added to the flask over 15 minutes and the mixture stirred by 1/2 hour. Dimethyl sulfate (108 gms; 81 mls; 0.86 mole) are added to the viscous mixture over a period of one hour and the reaction mixture becomes less thick as addition nears completion. When the addition is complete, the mixture is stirred for two hours. The reaction mixture is combined with 150 mls. of distilled water. The organic layer is washed three times with water and, after the addition of more diethyl ether, dried over MgSO4. Filtration and removal of solvent affords 50 gms. crude product (98.3% 4-methylphenyl-2-methoxyethyl ether). Distillation of the crude material yields pure 4-methylphenyl-2-methoxyethyl ether (B.P. 65° C. at 0.25 mm Hg). The infrared and proton nuclear magnetic resonance spectra are in agreement with the data presented in Example 1 and confirm the structure of the product.

Workup

  1. customFor this reaction, 50 gms
  2. customflask fitted with mechanical stirrer, condenser, addition funnel and N2 inlet
  3. additionthe reaction mixture becomes less thick as addition nears completion
  4. additionWhen the addition
  5. stirringthe mixture is stirred for two hours
  6. washThe organic layer is washed three times with water
  7. additionafter the addition of more diethyl ether
  8. dry with materialdried over MgSO4
  9. filtrationFiltration and removal of solvent
  10. customaffords 50 gms
  11. distillationDistillation of the crude material

Sources & evidence

ORD record
ord-447051ce03444e4392937e628bdb6e0c
Source dataset
uspto-grants-1987_12
Patent number
US04716146

Reaction notes

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