2,6-Dimethylphenol → 4-[1-(4-Bromo-3-methyl-phenyl)-1-ethyl-propyl]-2,6-dimethyl-phenol

HRID 546871Notes

Reaction equation

HRID 546871 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[OH:9].[Br:10][C:11]1[CH:16]=[CH:15][C:14]([C:17](O)([CH2:20][CH3:21])[CH2:18][CH3:19])=[CH:13][C:12]=1[CH3:23]>FC(F)(F)C(O)=O>[Br:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([C:6]2[CH:5]=[C:4]([CH3:8])[C:3]([OH:9])=[C:2]([CH3:1])[CH:7]=2)([CH2:20][CH3:21])[CH2:18][CH3:19])=[CH:13][C:12]=1[CH3:23]

Participants

4

Reactant 2

HCID 113352,6-DimethylphenolHCID 574330783-(4-Bromo-3-methyl-phenyl)-pentan-3-ol

Product 1

HCID 574847624-[1-(4-Bromo-3-methyl-phenyl)-1-ethyl-propyl]-2,6-dimethyl-phenolYield 93.2%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

2,6-Dimethylphenol (950 mg, 7.78 mmol) was added to a solution of 3-(4-bromo-3-methyl-phenyl)-pentan-3-ol (Example 38-(1); 2.0 g, 7.78 mmol) in trifluoroacetic acid (20 mL), and the mixture was stirred at room temperature for two hours. Then, the reaction mixture was concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=100:0 to 50:50) to give the target compound as a colorless oil (2.62 g, 93%).

Workup

  1. concentrationThen, the reaction mixture was concentrated under reduced pressure
  2. customThe resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=100:0 to 50:50)

Sources & evidence

ORD record
ord-0f4e489b9a234008b79b09a52ec8458d
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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