Ethyl Acetate → 5-Hexadecyloxymethyl-2-phenyl-1,3-dioxane

HRID 728494노트

반응식

HRID 728494 반응식
[OH:1][CH2:2][CH:3]1[CH2:8][O:7][CH:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[O:5][CH2:4]1.[H-].[Na+].CS(O[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])(=O)=O.C(OCC)(=O)C>C1C=CC=CC=1>[CH2:37]([O:1][CH2:2][CH:3]1[CH2:4][O:5][CH:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[O:7][CH2:8]1)[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH3:22]

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 519810Hexadecyl methanesulfonateHCID 10679342(2-Phenyl-1,3-dioxan-5-yl)methanol

생성물 1

HCID 198842025-Hexadecyloxymethyl-2-phenyl-1,3-dioxane수율 97%

시약·촉매·용매 1

HCID 241Benzene용매2회

반응 조건

온도
50 °C

실험 절차

A suspension of 7.769 g (40 mM) of 5-hydroxymethyl-2-phenyl-1,3-dioxane n1 and 2.08 g (52 mM) of 60% sodium hydride in oil in 150 ml of anhydrous benzene is heated at 50° C. for 1 hour then a solution of 17.28 g (54 mM) of n-hexadecyl methanesulfonate in 50 ml of anhydrous benzene is added. The reaction mixture is heated under refluxing for 7 hours. The product is isolated by ethyl acetate extraction. The ethyl acetate layer is washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and evaporated. Crystallization of the residue from n-pentane-methanol affords 16.203 g (97% yield) of the titled compound n2.

후처리

  1. temperatureThe reaction mixture is heated
  2. temperatureunder refluxing for 7 hours
  3. washThe ethyl acetate layer is washed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated
  6. customCrystallization of the residue from n-pentane-methanol

출처 및 근거

ORD 기록
ord-77066b4b4e9243eaa30cff8652522946
출처 데이터셋
uspto-grants-1991_09
특허 번호
US05047540

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