Glycerol → 1-[4-(trans-5-Hydroxydioxan-2-yl)phenyl]-4-pentylbicyclo[2.2.2]octane

HRID 635141

반응식

HRID 635141 반응식
[CH2:1]([C:6]12[CH2:13][CH2:12][C:9]([C:14]3[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][CH:15]=3)([CH2:10][CH2:11]1)[CH2:8][CH2:7]2)[CH2:2][CH2:3][CH2:4][CH3:5].[OH:22][CH2:23]C(CO)O.[C:28]1([CH3:34])C=CC=CC=1.C1(C)C=CC=CC=1.[OH2:42]>>[OH:42][C@@H:28]1[CH2:34][O:19][C@@H:18]([C:17]2[CH:20]=[CH:21][C:14]([C:9]34[CH2:8][CH2:7][C:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])([CH2:13][CH2:12]3)[CH2:11][CH2:10]4)=[CH:15][CH:16]=2)[CH2:23][O:22]1

참가 물질

5

반응물 4

HCID 753GlycerolHCID 1140TolueneHCID 212577614-(4-Pentylbicyclo[2.2.2]octyl)benzaldehydeHCID 22272177Toluene water

생성물 1

HCID 699632681-[4-(trans-5-Hydroxydioxan-2-yl)phenyl]-4-pentylbicyclo[2.2.2]octane수율 25%

실험 절차

A solution of 4-(4-pentylbicyclo[2.2.2]octyl)benzaldehyde (2.5 g, 8.5 mmol), glycerol (1.0 g, 8.5 mmol), pyridinium-(toluyl-4-sulphonate) (0.2 g) and toluene is heated for over 2 h so that the toluene/water mixture generated is continuously distilled off. The solution is evaporated down and the residue purified by column chromatography on silica gel using a 7:3 hexane/ethyl acetate mixture as eluent and recrystallisation from ethanol to yield 0.75 g (25%) of the 1-[4-(trans-5-hydroxydioxan-2-yl)phenyl]-4-pentylbicyclo[2.2.2]octane.

후처리

  1. distillationgenerated is continuously distilled off
  2. customThe solution is evaporated down
  3. customthe residue purified by column chromatography on silica gel using a 7:3 hexane/ethyl acetate mixture as eluent
  4. customrecrystallisation from ethanol

출처 및 근거

ORD 기록
ord-42a7e014ce5c4de19db69a73825416e0
출처 데이터셋
uspto-grants-2001_02
특허 번호
US06187393B1

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