Hydrochloric Acid → HCID 12832654, compound

HRID 1903430Notes

Reaction equation

HRID 1903430 reaction equation
C([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[C:21](=[O:22])[C:20]([O:23][CH3:24])=[C:19]([O:25][CH3:26])[C:18](=[O:27])[C:17]=1[CH3:28])(=O)C.Cl.C(=O)(O)[O-].[Na+]>CO>[OH:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[C:21](=[O:22])[C:20]([O:23][CH3:24])=[C:19]([O:25][CH3:26])[C:18](=[O:27])[C:17]=1[CH3:28]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 128326536-(11-Acetoxyundecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone

Product 1

HCID 12832654HCID 12832654, compoundYield 95.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution (200 ml) of 6-(11-acetoxyundecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone (4.2 g) in methanol is added concentrated hydrochloric acid (0.1 ml), and the mixture is allowed to stand at room temperature for 12 hours. To the reaction mixture is added sodium bicarbonate (0.2 g) and the solvent is distilled off. The product is dissolved in dichloromethane and the insoluble matter is filtered off. Removal of dichloromethane by distillation gives crude crystals. Recrystallization from hexane-ether (3:1) yields orange-yellow needles of 6-(11-hydroxyundecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone (I, n=11) (3.6 g) m.p. 57° C.

Workup

  1. distillationthe solvent is distilled off
  2. dissolutionThe product is dissolved in dichloromethane
  3. filtrationthe insoluble matter is filtered off
  4. customRemoval of dichloromethane
  5. distillationby distillation
  6. customgives crude crystals
  7. customRecrystallization from hexane-ether (3:1)

Sources & evidence

ORD record
ord-7ff19dfbb3b9447b8d1f941be238ccc2
Source dataset
uspto-grants-1984_03
Patent number
US04436753

Reaction notes

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