Water → 1,12-Bis-(12-bromododecyloxy)-dodecane

HRID 573030

반응식

HRID 573030 반응식
[H-].[Na+].[CH2:3]([OH:16])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][OH:15].Br[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][Br:30].O>CCCCCC.C1(C)C=CC=CC=1>[Br:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][O:16][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][Br:30]

참가 물질

7

반응물 4

HCID 962WaterHCID 187661,12-DibromododecaneHCID 24758Sodium hydrideHCID 797581,12-Dodecanediol

생성물 1

HCID 594992341,12-Bis-(12-bromododecyloxy)-dodecane수율 56%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8058Hexane용매

반응 조건

온도
80 °C

실험 절차

Sodium hydride (60%, 652 mg, 16.3 mmol) washed with hexane was suspended in toluene (3 ml), 1,12-dodecanediol (1.50 g, 7.41 mmol) was added, 1,12-dibromododecane (6.08 g, 18.5 mmol) was added, and the mixture was stirred at 80° C. for 4 days. The reaction mixture was cooled to room temperature, and pure water (30 ml) was added dropwise thereto in a water bath to quench the reaction. The mixture was extracted with chloroform (100 ml), and washed 3 times with 1N hydrochloric acid (30 ml), 3 times with 5% aqueous sodium hydrogen carbonate solution (30 ml), and once with 20% aqueous sodium chloride solution (30 ml). The organic layer was dried over sodium sulfate and the solvent of the filtrate was evaporated. The residue was isolated and purified by silica gel column chromatography, and precipitated with methanol (50 ml) to give 1,12-bis-(12-bromododecyloxy)-dodecane (yield 56%).

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customin a water bath to quench
  3. customthe reaction
  4. extractionThe mixture was extracted with chloroform (100 ml)
  5. washwashed 3 times with 1N hydrochloric acid (30 ml), 3 times with 5% aqueous sodium hydrogen carbonate solution (30 ml)
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. customthe solvent of the filtrate was evaporated
  8. customThe residue was isolated
  9. custompurified by silica gel column chromatography
  10. customprecipitated with methanol (50 ml)

출처 및 근거

ORD 기록
ord-a2a4c0fc4846452d909bdfb33c73885d
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029504B2

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