4-Bromophenol → 4-Bromo-2-(1,1-dimethyldecyl) phenol

HRID 345876Notes

Reaction equation

HRID 345876 reaction equation
[CH3:1][C:2]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[CH2:3].[Br:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1>>[Br:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([C:2]([CH3:1])([CH3:3])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH:15]=1

Participants

3

Reactant 2

HCID 78084-BromophenolHCID 876892-Methyl-1-undecene

Product 1

HCID 136335564-Bromo-2-(1,1-dimethyldecyl) phenol

Procedure

A mixture of 2-methyl-1-undecene (35.6 g, 211 mmoles), parabromphenol (36.6 g, 211 mmoles) and Dowex 50×12 resin (100-200 mesh) previously washed with water, rinsed with acetone and oven dried for 3 hours at 80° C., is heated at 100°-110° C. for 48 hours. The mixture is then cooled to ambient temperature and chromatographed on a silica column (eluant: a mixture of dichloromethane, 40% and hexane, 60%), yielding 4-bromo-2-(1,1-dimethyldecyl)-phenol in the form of a pale yellow oil. (30.85 g, 43%).

Workup

  1. washpreviously washed with water
  2. washrinsed with acetone and oven
  3. customdried for 3 hours at 80° C.
  4. temperatureis heated at 100°-110° C. for 48 hours
  5. customchromatographed on a silica column (eluant
  6. additiona mixture of dichloromethane, 40% and hexane, 60%),

Sources & evidence

ORD record
ord-20729f60a9f9451883f4a2f03ebb739f
Source dataset
uspto-grants-1991_10
Patent number
US05059621

Reaction notes

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