Phenol → 4-[1-(4-iodophenyl)-1,2-dimethylpropyl]Phenol

HRID 1025803Notes

Reaction equation

HRID 1025803 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](O)([CH:10]([CH3:12])[CH3:11])[CH3:9])=[CH:4][CH:3]=1.CC1C=CC(S(O)(=O)=O)=CC=1.[C:25]1([OH:31])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>>[I:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:28]2[CH:29]=[CH:30][C:25]([OH:31])=[CH:26][CH:27]=2)([CH3:9])[CH:10]([CH3:12])[CH3:11])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 996PhenolHCID 6101p-Toluenesulfonic acidHCID 590267482-(4-Iodophenyl)-3-methylbutan-2-ol

Product 1

HCID 590267534-[1-(4-iodophenyl)-1,2-dimethylpropyl]Phenol

Procedure

A mixture of 5a (56.0 g, 193 mmol), p-TSA (36.0 g, 193 mmol) and phenol (25.0 g, 251 mmol) was heated to 95 for 1 h. After cooling to room temperature, the reaction mixture was partitioned between DCM and water. The separated organic phase was washed with water, three times with saturated aqueous sodium bicarbonate, brine, dried (MgSO4) and concentrated in vacuo to afford the title compound 5b. This was used without further purification in the subsequent step.

Workup

  1. temperaturewas heated to 95 for 1 h
  2. customthe reaction mixture was partitioned between DCM and water
  3. washThe separated organic phase was washed with water, three times with saturated aqueous sodium bicarbonate, brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f874713af1574a12b8daf47ef560d639
Source dataset
uspto-grants-2014_05
Patent number
US08729104B2

Reaction notes

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