Diethyl Ether → HCID 13922667, compound

HRID 1588137Notes

Reaction equation

HRID 1588137 reaction equation
[CH3:1][O:2][C:3]1[C:4](=[O:39])[C:5]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH:18]2[O:38][CH:19]2[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]2[C:32](=[O:33])[C:31]([O:34][CH3:35])=[CH:30][C:29](=[O:36])[C:28]=2[OH:37])=[C:6]([OH:10])[C:7](=[O:9])[CH:8]=1.Cl(O)(=O)(=O)=[O:41].C(OCC)C>O1CCCC1>[CH3:35][O:34][C:31]1[C:32](=[O:33])[C:27]([CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH:19]([OH:41])[CH:18]([OH:38])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][C:5]2[C:4](=[O:39])[C:3]([O:2][CH3:1])=[CH:8][C:7](=[O:9])[C:6]=2[OH:10])=[C:28]([OH:37])[C:29](=[O:36])[CH:30]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 24247Perchloric AcidHCID 10437394HCID 10437394, compound

Product 1

HCID 13922667HCID 13922667, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

37 Milligrams of 1,16-bis(5-methoxy-2-hydroxy-1,4-benzoquinon-3-yl)-8,9-epoxyhexadecane was dissolved in 2 ml of tetrahydrofuran, to this solution was added 0.5 ml of 5% perchloric acid aqueous solution and the mixture was stirred at room temperature for 4 hours. Then, 30 ml of diethyl ether was added to the reaction mixture, and the organic layer was washed with a saturated sodium chloride aqueous solution in several times, and dried over anhydrous sodium sulfate. This extract was purified by means of a preparative thin layer chromatography [adsorbent: "Silica gel 60 F254 " manufactured by E. Merck A. G., developing solvent: chloroform-methanol (85:15 mixture by volume/volume)], then recrystallized from ethyl acetate-n-hexane to obtain 12 mg of 1,16-bis(5-methoxy-2-hydroxy-1,4-benzoquinon-3-yl)-8,9-dihydroxyhexadecane. Yellow powdery crystals.

Workup

  1. washthe organic layer was washed with a saturated sodium chloride aqueous solution in several times
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThis extract was purified by means of a preparative thin layer chromatography [adsorbent: "Silica gel 60 F254 " manufactured by E. Merck A. G., developing solvent: chloroform-methanol (85:15 mixture by volume/volume)]
  4. customrecrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-e97a065418ee4d878aebe2a955879d73
Source dataset
uspto-grants-1993_06
Patent number
US05220042

Reaction notes

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