Diethyl Ether → 2-(4-Iodophenyl)propan-2-ol

HRID 328521Notes

Reaction equation

HRID 328521 reaction equation
C(OC(=O)[C:5]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][CH:6]=1)C.CC[O:15][CH2:16][CH3:17].[CH3:18][Mg]Br>O>[CH3:18][C:16]([OH:15])([CH3:17])[C:5]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 142891Ethyl 4-iodobenzoateHCID 178418573HCID 178418573, compound

Product 1

HCID 539961442-(4-Iodophenyl)propan-2-ol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2.76 grams of ethyl-4-iodobenzoate in 10 ml. of ether is placed in a dry flask. The solution is cooled in an ice bath and is stirred. Over a 5-minute period, 26.5 ml. of a 1.52 M ethereal solution of methyl magnesium bromide is added. The solution is stirred for 3 hours while in the ice bath. Water (6 ml.) is added dropwise while stirring. The solution is filtered and the filter cake is washed with six 20 ml. portions of ether. The combined ether phases are dried over magnesium sulfate and filtered. Removal of the ether gives α,α-dimethyl-4-iodobenzyl alcohol as a clear, light yellow liquid.

Workup

  1. temperatureThe solution is cooled in an ice bath
  2. waitOver a 5-minute period, 26.5 ml
  3. stirringwhile stirring
  4. filtrationThe solution is filtered
  5. washthe filter cake is washed with six 20 ml
  6. dry with materialThe combined ether phases are dried over magnesium sulfate
  7. filtrationfiltered
  8. customRemoval of the ether

Sources & evidence

ORD record
ord-8abdc95a00f247eaa1ad703d32838bb9
Source dataset
uspto-grants-1977_04
Patent number
US04017543

Reaction notes

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