1-Bromododecane → 2,5-Dibromo-4-(dodecyloxy)phenol

HRID 643181Notes

Reaction equation

HRID 643181 reaction equation
[Br:1][C:2]1[CH:8]=[C:7]([OH:9])[C:6]([Br:10])=[CH:5][C:3]=1[OH:4].[OH-].[Na+].[CH2:13](Br)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>C(O)C>[Br:1][C:2]1[CH:8]=[C:7]([O:9][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH3:13])[C:6]([Br:10])=[CH:5][C:3]=1[OH:4]

Participants

5

Reactant 3

HCID 89191-BromododecaneHCID 14798Sodium HydroxideHCID 2809452,5-Dibromohydroquinone

Product 1

HCID 667607252,5-Dibromo-4-(dodecyloxy)phenolYield 60%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
55 °C

Procedure

2,5-Dibromohydroquinone 3 (40.2 g, 0.15 mol) was dissolved in a solution of sodium hydroxide (9.2 g, 0.23 mol) in 1.5 L of absolute ethanol at room temperature under nitrogen atmosphere. The reaction mixture was warmed to 50-60° C. with constant stirring. The dodecylbromide (36 ml, 0.15 mol) was added drop wise to the above reaction mixture at 60° C. After 10 h of stirring under nitrogen atmosphere, the reaction mixture was cooled and the precipitate formed was filtered and washed with methanol. This precipitate was identified as dialleylated-2,5-dibromohydroquinone as a side product. The filtrate was evaporated to remove the solvent. 2 L of distilled water was added to the residue and the mixture was acidified with 36% HCl, boiled gently for 1 h and cooled. The resulting precipitate was collected by filtration, washed with water and dried in vacuo. The crude product was purified by column chromatography using a mixture of solvents (CH2Cl2: hexanes, 4:6) to get the pure product in 60% yield.

Workup

  1. temperaturethe reaction mixture was cooled
  2. customthe precipitate formed
  3. filtrationwas filtered
  4. washwashed with methanol
  5. customThe filtrate was evaporated
  6. customto remove the solvent
  7. addition2 L of distilled water was added to the residue
  8. waitboiled gently for 1 h
  9. temperaturecooled
  10. filtrationThe resulting precipitate was collected by filtration
  11. washwashed with water
  12. customdried in vacuo
  13. customThe crude product was purified by column chromatography
  14. additiona mixture of solvents (CH2Cl2: hexanes, 4:6)
  15. customto get the pure product in 60% yield

Sources & evidence

ORD record
ord-696af86c369949ada4c717ca3814bfb5
Source dataset
uspto-grants-2010_04
Patent number
US07700040B2

Reaction notes

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