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

HRID 859867Notes

Reaction equation

HRID 859867 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-bbbbdaf83d294eb0b695be71a98cabaa
Source dataset
uspto-grants-2006_12
Patent number
US07153850B2

Reaction notes

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