2-Bromopropane → Isopropyl 2-isopropylphenyl ether

HRID 543911Notes

Reaction equation

HRID 543911 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])([CH3:3])[CH3:2].C[O-].[Na+].[Na].[CH:15](Br)([CH3:17])[CH3:16]>CO>[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][CH:15]([CH3:17])[CH3:16])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 63582-BromopropaneHCID 69432-IsopropylphenolHCID 5360545SodiumHCID 10942334Sodium Methoxide

Product 1

HCID 13531071Isopropyl 2-isopropylphenyl ether

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 2-isopropylphenol (75 g, 0.54 mol) in 60 ml methanol was added, under nitrogen, to a solution of sodium methoxide, prepared by reacting 13.1 g (0.57 mol) sodium with 150 ml dry methanol. To this stirred solution was added isopropyl bromide (82.2 g, 0.66 mol) dropwise over several hours, after which the reaction mixture was heated at reflux overnight. The cooled mixture was filtered to remove solids and methanol was removed on a rotary evaporator. The residue, containing both liquid and solid, was treated with about equal volumes of diethyl ether and water, with the aqueous phase then separated and discarded. The ether phase was washed with Claisen solution, water being added to facilitate separation of phases, and the organic phase retained. The combined aqueous phases was extracted with ether, the extract being added to the prior retained organic phase, and the combined material was dried over anhydrous magnesium sulfate. Ether was removed by evaporation and the residue was distilled to afford isopropyl (2-isopropylphenyl) ether.

Workup

  1. customprepared
  2. temperatureafter which the reaction mixture was heated
  3. temperatureat reflux overnight
  4. filtrationThe cooled mixture was filtered
  5. customto remove solids and methanol
  6. customwas removed on a rotary evaporator
  7. additionThe residue, containing both liquid and solid
  8. additionwas treated with about equal volumes of diethyl ether and water, with the aqueous phase
  9. customthen separated
  10. washThe ether phase was washed with Claisen solution, water being
  11. additionadded
  12. customseparation of phases
  13. extractionThe combined aqueous phases was extracted with ether
  14. additionthe extract being added to the prior retained organic phase
  15. dry with materialthe combined material was dried over anhydrous magnesium sulfate
  16. customEther was removed by evaporation
  17. distillationthe residue was distilled

Sources & evidence

ORD record
ord-2ad9b341e0a941f6a484da5bf2cca7f5
Source dataset
uspto-grants-1984_05
Patent number
US04447657

Reaction notes

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