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

HRID 604227노트

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HRID 604227 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
55 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-06ee73f1ada54861aa273a79f0faf6a5
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07910058B2

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