2,6-Di-tert-butyl-4-methylphenol → Phenol, 4-(bromomethyl)-2,6-bis(1,1-dimethylethyl)-

HRID 976233

Reaction equation

HRID 976233 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:6]=1[OH:16])([CH3:4])([CH3:3])[CH3:2].[Br:17]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[C:12]([C:7]1[CH:8]=[C:9]([CH2:11][Br:17])[CH:10]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:6]=1[OH:16])([CH3:15])([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 314042,6-Di-tert-butyl-4-methylphenolHCID 67184N-bromobutanimide

Product 1

HCID 612973Phenol, 4-(bromomethyl)-2,6-bis(1,1-dimethylethyl)-

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 1 g of 2,6-di-t-butyl-4-methyl phenol, 0.9 g of N-bromosuccinimide and 40 ml of carbon tetrachloride was boiled for 1.5 hours. Succinimide was removed by filtration, and the resulting organic solution was evaporated to give a viscous liquid with the following 1H NMR spectrum (CDCl3, ppm from TMS): 7.05 ppm (s, ArH, 2), 5,15 ppm (s, OH, 1), 4.35 ppm (s, CH2Br, 2) and 1.3 ppm (s, CH3, 18).

Workup

  1. customSuccinimide was removed by filtration
  2. customthe resulting organic solution was evaporated
  3. customto give a viscous liquid with the following 1H NMR spectrum (CDCl3, ppm from TMS): 7.05 ppm (s, ArH, 2), 5,15 ppm (s, OH, 1), 4.35 ppm (s, CH2Br, 2) and 1.3 ppm (s, CH3, 18)

Sources & evidence

ORD record
ord-2090368da56045f2874063feeb30f5d0
Source dataset
uspto-grants-1997_03
Patent number
US05612321

Linked notes

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