HCID 178493904, compound → HCID 178493903, compound

HRID 330552Notes

Reaction equation

HRID 330552 reaction equation
C([O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]2[C:21](=[O:22])[C:20]([O:23][CH3:24])=[C:19]([O:25][CH3:26])[C:18](=[O:27])[C:17]=2[CH3:28])[CH2:7][CH2:6]1)(=O)C>Cl.CO>[OH:4][C@H:5]1[CH2:10][CH2:9][C@H:8]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]2[C:21](=[O:22])[C:20]([O:23][CH3:24])=[C:19]([O:25][CH3:26])[C:18](=[O:27])[C:17]=2[CH3:28])[CH2:7][CH2:6]1

Participants

3

Reactant 1

HCID 178493904HCID 178493904, compound

Product 1

HCID 178493903HCID 178493903, compound

Reagents, catalysts & solvents 1

HCID 21893726Hydrochloride methanolSolvent

Procedure

trans-6-[5-(4-Acetoxycyclohexyl)pentyl]-2,3-dimethoxy-5-methyl-1,4-benzoquinone (0.415 g) is dissolved in hydrochloric acid-methanol (1.180, 10 ml), and the mixture is stirred at room temperature for 24 hours. The solvent is distilled off under reduced pressure, and the residue is dissolved in ether, washed with aqueous sodium hydrogen carbonate and then with water and dried. The ether is distilled off and the residue is subjected to silica gel column chromatography. Recrystallization of the desired fractions from ether-hexane gives trans-6-[5-(4-hydroxycyclohexyl)pentyl]-2,3-dimethoxy-5-methyl-1,4-benzoquinone as orange needles, m.p. 64°-65° C.

Workup

  1. distillationThe solvent is distilled off under reduced pressure
  2. dissolutionthe residue is dissolved in ether
  3. washwashed with aqueous sodium hydrogen carbonate
  4. dry with materialwith water and dried
  5. distillationThe ether is distilled off
  6. customRecrystallization of the desired fractions from ether-hexane

Sources & evidence

ORD record
ord-ee0f2f7f051748a8b5459f10e2d42cdf
Source dataset
uspto-grants-1990_01
Patent number
US04897420

Reaction notes

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