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

HRID 637889Notes

Reaction equation

HRID 637889 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 of 6-(12-acetoxydodecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone (4.4 g) in methanol (200 ml) is added concentrated hydrochloric acid (0.1 ml) and the mixture is kept standing at room temperature for 12 hours. To the reaction mixture is added sodium hydrogen carbonate (0.2 g), and the solvent is distilled off. The residue is dissolved in dichloromethane and the insoluble materials are filtered off. Dichloromethane is distilled off to thereby leave crude crystals. Recrystallization from hexane-ether (3:1) gives 6-(12-hydroxydodecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone (3.8 g) as orange-yellow needles. Melting point: 63° C.

Workup

  1. distillationthe solvent is distilled off
  2. dissolutionThe residue is dissolved in dichloromethane
  3. filtrationthe insoluble materials are filtered off
  4. distillationDichloromethane is distilled off
  5. customto thereby leave crude crystals
  6. customRecrystallization from hexane-ether (3:1)

Sources & evidence

ORD record
ord-2e84efc9d7814917ae87e22463189bd5
Source dataset
uspto-grants-1985_12
Patent number
US04559177

Reaction notes

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