3-Isopropylphenol → 4-Chloro-3-isopropylphenol

HRID 81750Notes

Reaction equation

HRID 81750 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)([CH3:3])[CH3:2].C(O[Cl:16])(C)(C)C>C1C=CC=CC=1.C(Cl)(Cl)Cl>[Cl:16][C:7]1[CH:8]=[CH:9][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:5][C:6]=1[OH:10].[Cl:16][C:9]1[CH:8]=[CH:7][C:6]([OH:10])=[CH:5][C:4]=1[CH:1]([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 120593-IsopropylphenolHCID 521297Tert-Butyl hypochlorite

Product 2

HCID 183278444-Chloro-3-isopropylphenolYield 104.4%HCID 595964872-Chloro-5-isopropylphenol

Reagents, catalysts & solvents 1

HCID 22101329Benzene--trichloromethane (1/1)Solvent

Procedure

A solution of 3-isopropyl phenol (10.0 g, 73.4 mmol) in 350 mL 9:1 benzene/CHCl3 was cooled to 0° C. Hypochlorous acid tert-butyl ester (8.77 g, 80.8 mmol) was added drop-wise over 5 min and the mixture was allowed to warm to rt. After 16 h the mixture was concentrated in vacuo to give a crude oil. Purification via flash chromatography afforded 2-chloro-5-isopropyl-phenol and 4-chloro-3-isopropyl-phenol (6.540 g, 52%) as a 7:3 inseparable mixture of isomers in the form of a pale yellow oil. The combined regioisomers were used together in the following step.

Workup

  1. concentrationAfter 16 h the mixture was concentrated in vacuo
  2. customto give a crude oil
  3. customPurification via flash chromatography

Sources & evidence

ORD record
ord-d4f92e425b384e89918a54bc9c5a3d56
Source dataset
uspto-grants-2014_09
Patent number
US08846705B2

Reaction notes

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