4-Benzylphenol → 4-Benzyl-2-chlorophenol

HRID 2254563Notes

Reaction equation

HRID 2254563 reaction equation
[CH2:1]([C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:15]OC(C)(C)C>C(Cl)(Cl)(Cl)Cl>[CH2:1]([C:8]1[CH:9]=[CH:10][C:11]([OH:14])=[C:12]([Cl:15])[CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 75634-BenzylphenolHCID 521297Tert-Butyl hypochlorite

Product 1

HCID 950944-Benzyl-2-chlorophenolYield 94.3%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

18.4 g of 4-benzylphenol was dissolved in 100 ml of carbon tetrachloride and thereto was added dropwise 10.85 g of t-butyl hypochlorite at -5°-0° C. with stirring. After stirring for 3 hours at room temperature, the reaction mixture was washed with a saturated aqueous sodium hydrogen-carbonate solution and then with water, then dried over anhydrous magnesium sulfate and thereafter, concentrated under reduced pressure. The resulting oily residue was chromatographed on a silica gel column (eluting solvent hexane : acetone=3 : 1 (v/v)) to obtain 20.6 g of 4-benzyl-2-chlorophenol.

Workup

  1. stirringAfter stirring for 3 hours at room temperature
  2. washthe reaction mixture was washed with a saturated aqueous sodium hydrogen-carbonate solution
  3. dry with materialwith water, then dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting oily residue was chromatographed on a silica gel column (eluting solvent hexane : acetone=3 : 1 (v/v))

Sources & evidence

ORD record
ord-afd480d5b75b4a209ef87f6ddd146554
Source dataset
uspto-grants-1993_08
Patent number
US05236924

Reaction notes

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