Glycerol → 2-Heptadecyl 2-methyl 4-hydroxymethyl 1,3-dioxolan

HRID 1649770

반응식

HRID 1649770 반응식
[CH3:1][C:2](=[O:20])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].[OH:21][CH2:22][CH:23]([CH2:25]O)[OH:24].C1(C)C=CC(S(O)(=O)=O)=CC=1.O1CCOC1>C1(C)C=CC=CC=1.O>[CH2:3]([C:2]1([CH3:1])[O:24][CH:23]([CH2:22][OH:21])[CH2:25][O:20]1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

참가 물질

7

반응물 4

HCID 753GlycerolHCID 6101p-Toluenesulfonic acidHCID 125861,3-Dioxolane2회HCID 694232-Nonadecanone

생성물 1

HCID 143739382-Heptadecyl 2-methyl 4-hydroxymethyl 1,3-dioxolan

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매

실험 절차

In an appropriate reactor were poured 11.1 g (40 mmol) of 2-nonadecanone, 6 g--which represents an excess with regard to the stoichiometric proportions--of twice distilled glycerol and 0.6 g of p-toluenesulphonic acid dissolved in 120 ml of dry toluene. The reaction mixture was refluxed under stirring for 12 hours and the resulting water was eliminated using a Dean Stark apparatus. After cooling, the organic phase was washed with 30 ml of 5% by weight aqueous solution of potassium hydroxide and then three times with the minimum amount of water. After drying over anhydrous sodium sulphate, the solvent was removed under reduced pressure. The residue was then purified by chromatography on a silica gel column. There were successively eluted the fraction of the ketone not involved in the reaction (petroleum ether : diethyl ether, 95:5 by volume), and then the dioxolan a (petroleum ether/diethyl ether 85:15 by volume). the dioxolan is a viscous product, partially crystallized.

후처리

  1. temperatureThe reaction mixture was refluxed
  2. temperatureAfter cooling
  3. washthe organic phase was washed with 30 ml of 5% by weight aqueous solution of potassium hydroxide
  4. dry with materialAfter drying over anhydrous sodium sulphate
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was then purified by chromatography on a silica gel column
  7. washThere were successively eluted the fraction of the ketone not
  8. custominvolved in the reaction (petroleum ether : diethyl ether, 95:5 by volume)
  9. custompartially crystallized

출처 및 근거

ORD 기록
ord-355692afefd94f76b379398f93ebe204
출처 데이터셋
uspto-grants-1990_05
특허 번호
US04921865

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