Benzyl Bromide → HCID 60026622, compound

HRID 400637Notes

Reaction equation

HRID 400637 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([C:12]([CH3:17])([CH3:16])[CH2:13][CH2:14][OH:15])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:18]([O:11][C:8]1[CH:9]=[CH:10][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:6][C:7]=1[C:12]([CH3:17])([CH3:16])[CH2:13][CH2:14][OH:15])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 60026402HCID 60026402, compound

Product 1

HCID 60026622HCID 60026622, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-tert-butyl-2-(3-hydroxy-1,1-dimethylpropyl)phenol (2 g, 8.5 mmol) and 1.1 mL benzyl bromide in 10 mL of DMF was added 1.75 g of potassium carbonate (K2CO3) and the reaction mixture stirred at room temperature until TLC indicated that the reaction was complete. After stirring overnight, the reaction mixture was diluted with ice and extracted with diethyl ether. The organics were combined, washed four times with water, washed with brine, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified on COMBIFLASH® apparatus (0% to 30% ethyl acetate-hexanes) to give 1.7 g of 3-(2-benzyloxy-5-tert-butylphenyl)-3-methylbutan-1-ol as an oil.

Workup

  1. stirringAfter stirring overnight
  2. additionthe reaction mixture was diluted with ice
  3. extractionextracted with diethyl ether
  4. washwashed four times with water
  5. washwashed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified on COMBIFLASH® apparatus (0% to 30% ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-25f0f5fa79a44bd1888511af546024b1
Source dataset
uspto-grants-2014_06
Patent number
US08741897B2

Reaction notes

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