Tert-Butyl hypochlorite → 2-Chloro-4-sec-butoxyphenol

HRID 1463916Notes

Reaction equation

HRID 1463916 reaction equation
[CH:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1)([CH2:3][CH3:4])[CH3:2].C(O[Cl:18])(C)(C)C>C(Cl)(Cl)(Cl)Cl>[CH:1]([O:5][C:6]1[CH:7]=[CH:8][C:9]([OH:12])=[C:10]([Cl:18])[CH:11]=1)([CH2:3][CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 521297Tert-Butyl hypochloriteHCID 138820044-(1-Methyl-1-propyloxy)-phenol

Product 1

HCID 229187772-Chloro-4-sec-butoxyphenolYield 88.1%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 5.0 g of 4-sec-butoxyphenol in 50 ml of carbon tetrachloride, there was added dropwise 3.27 g of t-butylhypochlorite with vigorously stirring and ice-cooling. After completion of the addition, the reaction mixture was stirred at room temperature for 5 hours and concentrated, followed by addition of 200 ml of ethyl acetate. The obtained solution was washed with an agueous solution of 5% wt. sodium dicarbonate, dried and concentrated under reduced pressure. The residue was subjected to silica gel chromatography to give 5.32 g of 4-sec-butoxy-2-chlorophenol. Yield. 88%. nD23.5 1.5312.

Workup

  1. temperatureice-cooling
  2. additionAfter completion of the addition
  3. stirringthe reaction mixture was stirred at room temperature for 5 hours
  4. concentrationconcentrated
  5. additionfollowed by addition of 200 ml of ethyl acetate
  6. washThe obtained solution was washed with an agueous solution of 5% wt. sodium dicarbonate
  7. customdried
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3a41a93129e244a18c9f17092e697b4b
Source dataset
uspto-grants-1994_04
Patent number
US05302619

Reaction notes

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