4-tert-Butylphenol → 4-tert-Butyl-2-chlorophenol

HRID 1867242Notes

Reaction equation

HRID 1867242 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].S(Cl)([Cl:15])(=O)=O>ClCCl>[Cl:15][C:9]1[CH:10]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:6]=[CH:7][C:8]=1[OH:11]

Participants

4

Reactant 2

HCID 73934-tert-ButylphenolHCID 24648Sulfuryl chloride

Product 1

HCID 73804-tert-Butyl-2-chlorophenolYield 148.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-t-Butylphenol (2.76 g, 18.4 mmol) was dissolved in dichloromethane (25 ml). Sulfuryl chloride (1.6 ml, 9.9 mmol) was added dropwise to the obtained solution, and they were stirred at room temperature for 3 days and then concentrated under reduced pressure. After the purification by the silica gel column chromatography, 2-chloro-4-t-butylphenol (yield: 2.71 g, 80%) was obtained.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customAfter the purification by the silica gel column chromatography

Sources & evidence

ORD record
ord-4f09ae02871b45c19a221062961ffc1e
Source dataset
uspto-grants-2009_12
Patent number
US07632830B2

Reaction notes

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