Hydrochloric Acid → 6-(12-Hydroxydodecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone

HRID 1903432Notes

Reaction equation

HRID 1903432 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][CH2:16][C:17]1[C:22](=[O:23])[C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[C:19](=[O:28])[C:18]=1[CH3:29])(=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][CH2:16][C:17]1[C:22](=[O:23])[C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[C:19](=[O:28])[C:18]=1[CH3:29]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 128814656-(12-Acetoxydodecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone

Product 1

HCID 128814646-(12-Hydroxydodecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinoneYield 96.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution (200 ml) of 6-(12-acetoxydodecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone (4.4 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 this reaction mixture is added sodium bicarbonate (0.2 g), and the solvent is distilled off. The product is dissolved in dichloromethane, the insoluble matter is filtered off and the dichloromethane is distilled off to give crude crystals. Recrystallization from hexane-ether (3:1) gives orange-yellow needles of 6-(12-hydroxydodecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone (3.8 g). m.p. 63° C.

Workup

  1. distillationthe solvent is distilled off
  2. dissolutionThe product is dissolved in dichloromethane
  3. filtrationthe insoluble matter is filtered off
  4. distillationthe dichloromethane is distilled off
  5. customto give crude crystals
  6. customRecrystallization from hexane-ether (3:1)

Sources & evidence

ORD record
ord-52482bebd13f4e48abe6f5271c6890e5
Source dataset
uspto-grants-1984_03
Patent number
US04436753

Reaction notes

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