1,6-Dibromohexane → 12-Bromo-3-methyl-6-oxadodecan-1-ol

HRID 617274

반응식

HRID 617274 반응식
[CH3:1][CH:2]([CH2:6][CH2:7][OH:8])[CH2:3][CH2:4][OH:5].[Br:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]Br.[H-].[Na+].[Cl-].[NH4+]>O1CCOCC1.O>[Br:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][O:5][CH2:4][CH2:3][CH:2]([CH3:1])[CH2:6][CH2:7][OH:8]

참가 물질

7

반응물 4

HCID 123681,6-DibromohexaneHCID 205243-Methyl-1,5-pentanediolHCID 24758Sodium hydrideHCID 25517Ammonium Chloride

생성물 1

HCID 1106586012-Bromo-3-methyl-6-oxadodecan-1-ol수율 65.1%

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

118 g (1.0 mol) of 3-methyl-1,5-pentanediol and 317 g (1.3 mol) of 1,6-di-bromohexane in 2.5 l of dioxan were treated at room temperature with 28 g (1.1 mol) of 95 percent sodium hydride and subsequently heated under reflux for 24 h. After cooling the reaction mixture was treated with 400 ml of water, neutralized with saturated ammonium chloride solution and subsequently extracted three times with 1 l of tert-butyl methyl ether each time. The combined organic extracts were washed with saturated ammonium chloride solution, dried over magnesium sulphate and concentrated on a rotary evaporator. Starting material and byproducts were removed by distillation in a vacuum at 150° C. bath temperature and 0.09 mbar. As the distillation residue there were obtained 183 g of 66 percent 12-bromo-3-methyl-6-oxadodecan-1-ol (43%), which is sufficiently pure for the further reactions.

후처리

  1. temperaturesubsequently heated
  2. temperatureunder reflux for 24 h
  3. temperatureAfter cooling the reaction mixture
  4. extractionsubsequently extracted three times with 1 l of tert-butyl methyl ether each time
  5. washThe combined organic extracts were washed with saturated ammonium chloride solution
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated on a rotary evaporator
  8. customStarting material and byproducts were removed by distillation in a vacuum at 150° C. bath temperature and 0.09 mbar

출처 및 근거

ORD 기록
ord-61bebb9fccbc45e99a9e77bd6691e0eb
출처 데이터셋
uspto-grants-1999_09
특허 번호
US05948812

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