Hydrochloric Acid → 2,3,6,7,10,11-Hexa-{(s)-2-octyloxycarbonyloxy}triphenylene

HRID 1066698Notes

Reaction equation

HRID 1066698 reaction equation
[OH:1][C:2]1[C:19]([OH:20])=[CH:18][C:17]2[C:16]3[C:11](=[CH:12][C:13]([OH:22])=[C:14]([OH:21])[CH:15]=3)[C:10]3[C:5](=[CH:6][C:7]([OH:24])=[C:8]([OH:23])[CH:9]=3)[C:4]=2[CH:3]=1.[C:25](Cl)(=[O:35])[O:26][C@H:27]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH3:28].Cl>N1C=CC=CC=1>[CH3:28][C@H:27]([O:26][C:25]([O:1][C:2]1[C:19]([O:20][C:25]([O:26][C@H:27]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH3:28])=[O:35])=[CH:18][C:17]2[C:16]3[C:11](=[CH:12][C:13]([O:22][C:25]([O:26][C@H:27]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH3:28])=[O:35])=[C:14]([O:21][C:25]([O:26][C@H:27]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH3:28])=[O:35])[CH:15]=3)[C:10]3[C:5](=[CH:6][C:7]([O:24][C:25]([O:26][C@H:27]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH3:28])=[O:35])=[C:8]([O:23][C:25]([O:26][C@H:27]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH3:28])=[O:35])[CH:9]=3)[C:4]=2[CH:3]=1)=[O:35])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10899487(s)-2-Octyl chlorocarbonateHCID 110886102,3,6,7,10,11-Hexahydroxytriphenylene

Product 1

HCID 206611922,3,6,7,10,11-Hexa-{(s)-2-octyloxycarbonyloxy}triphenyleneYield 69%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A TFT solution of 4.86 g (15 mmol) of 2,3,6,7,10,11-hexahydroxytriphenylene and 135 mmol of (s)-2-octyl chlorocarbonate was stirred while chilled with ice. After 40 ml of pyridine was slowly and dropwise added, the liquid was heated for 50 minutes to the room temperature. The solution was poured into diluted hydrochloric acid, and the resulting mixture was extracted with ethyl acetate. The organic phase was collected, washed with diluted hydrochloric acid, water and saturated aqueous solution of sodium chloride, and then dried with anhydrous magnesium sulfate. After the solvent was distilled off, the obtained brown oily product (26.2 g) was purified through silica-gel chromatography (hexane:ethyl acetate =10:1) to prepare 13.75 g of the titled optically active triphenylene compound (5) [colorless oily product at room temperature, yield: 69%].

Workup

  1. temperaturewhile chilled with ice
  2. additiondropwise added
  3. extractionthe resulting mixture was extracted with ethyl acetate
  4. customThe organic phase was collected
  5. washwashed with diluted hydrochloric acid, water and saturated aqueous solution of sodium chloride
  6. dry with materialdried with anhydrous magnesium sulfate
  7. distillationAfter the solvent was distilled off
  8. customthe obtained brown oily product (26.2 g) was purified through silica-gel chromatography (hexane:ethyl acetate =10:1)
  9. customto prepare 13.75 g of the

Sources & evidence

ORD record
ord-08296222045147deaf5c7fe3b59b7ca0
Source dataset
uspto-grants-2001_06
Patent number
US06245398B1

Reaction notes

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