Tert-Butyl hypochlorite → 4-(1-(4-Isopropyloxyphenyl)-1-methylethyl)-2-chlorophenol

HRID 260790Notes

Reaction equation

HRID 260790 reaction equation
[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)([CH3:13])[CH3:12])=[CH:7][CH:6]=1)([CH3:3])[CH3:2].[Cl:21]OC(C)(C)C>C(Cl)(Cl)(Cl)Cl>[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([Cl:21])[CH:15]=2)([CH3:13])[CH3:12])=[CH:7][CH:6]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 521297Tert-Butyl hypochloriteHCID 214662204-(1-(4-Isopropyloxyphenyl)-1-methylethyl)phenol

Product 1

HCID 214663674-(1-(4-Isopropyloxyphenyl)-1-methylethyl)-2-chlorophenolYield 85.2%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 4-(1-(4-isopropyloxyphenyl)-1-methylethyl)phenol (0.51 g) in carbon tetrachloriode (1.3 ml), a solution prepared by dissolving 0.23 g of tert-butyl hypochlorite in 0.5 ml of carbon tetrachloride was added dropwise with stirring under ice cooling. After 30 minutes, an ice bath was removed, and the mixture was stirred at room temperature for 30 minutes. The reaction solution was poured into water and extracted three times with 5 ml of carbon tetrachloride. Then, the carbon tetrachloride layers were combined, washed with water, dried over anhydrous magnesium sulfate and then concentrated to give a crude product. This crude product was subjected to silica gel column chromatography to give 0.49 g of 4-(1-(4-isopropyloxyphenyl)-1-methylethyl)-2-chlorophenol (yield, 85%).

Workup

  1. additionwas added dropwise
  2. customan ice bath was removed
  3. stirringthe mixture was stirred at room temperature for 30 minutes
  4. additionThe reaction solution was poured into water
  5. extractionextracted three times with 5 ml of carbon tetrachloride
  6. washwashed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. customto give a crude product

Sources & evidence

ORD record
ord-e2c8039c4f724ea49831a6906ee792a9
Source dataset
uspto-grants-1996_06
Patent number
US05530015

Reaction notes

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