Sulfuric Acid → 12-Cyclohexyldodecyl bromide

HRID 478098

반응식

HRID 478098 반응식
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][Br:14].[CH:15]1([Mg]Br)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.S(=O)(=O)(O)O.C(OCC)(=O)C>O1CCCC1.[Li+].[Li+].[Cl-].[Cl-].[Cl-].[Cl-].[Cu+2]>[CH:15]1([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][Br:14])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

참가 물질

7

반응물 4

HCID 1118Sulfuric AcidHCID 8857Ethyl AcetateHCID 187661,12-DibromododecaneHCID 178419651HCID 178419651, 화합물

생성물 1

HCID 1487772112-Cyclohexyldodecyl bromide수율 40.2%

시약·촉매·용매 2

HCID 193501Copper;dilithium;tetrachloride촉매HCID 8028Tetrahydrofuran용매2회

실험 절차

To 98 g (0.30 mole) of 1,12-dibromododecane in 300 ml of anhydrous tetrahydrofuran (THF), cyclohexyl magnesium bromide (0.30 mole) in 300 ml of THF was added dropwise at 10°-15° C. over a period of 1.5 hours in the presence of 0.5 mole percent of dilithium tetrachlorocuprate (Li2CuCl4), and the mixture was stirred at room temperature overnight. To the reaction mixture 16 ml of 2N sulfuric acid was added until pH became about 2, and about 500 ml of ethyl acetate was added. The insoluble material was filtrated off, and the filtrate was washed with water, saturated aqueous solution of sodium hydrogencarbonate, and water, successively, and dried over anhydrous magnesium sulfate. The organic layer was concentrated under reduced pressure, and the resulting oil was subjected to distillation under reduced pressure. The distillate having a boiling point of 166°-167° C. (0.3 mm Hg) was collected, to give 40 g (40%) of the above-captioned compound.

후처리

  1. additionwas added
  2. filtrationThe insoluble material was filtrated off
  3. washthe filtrate was washed with water, saturated aqueous solution of sodium hydrogencarbonate, and water
  4. dry with materialsuccessively, and dried over anhydrous magnesium sulfate
  5. concentrationThe organic layer was concentrated under reduced pressure
  6. distillationthe resulting oil was subjected to distillation under reduced pressure
  7. customwas collected

출처 및 근거

ORD 기록
ord-3ac1593b5a344b1294358cb833b30665
출처 데이터셋
uspto-grants-1989_12
특허 번호
US04889953

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