Sulfuric Acid → HCID 12832654, compound

HRID 637892Notes

Reaction equation

HRID 637892 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.S(=O)(=O)(O)O.C(=O)([O-])O.[K+]>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 1118Sulfuric AcidHCID 516893Potassium 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 of 6-(11-acetoxyundecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone (4.2 g) in methanol (200 ml) is added concentrated sulfuric acid (0.1 ml) and the mixture is kept standing at room temperature for 12 hours. To a reaction mixture is added potassium hydrogencarbonate (0.2 g) and the solvent is distilled off. The resultant is dissolved in dichloromethane and insolubles are filtered off. Dichloromethane is distilled off to leave crude crystals. Recrystallization from hexane-ether (3:1) gives 6-(11-hydroxyundecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone (3.6 g) as orange-yellow needles. m.p.: 57° C.

Workup

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

Sources & evidence

ORD record
ord-28170f8417d442e9b2372b0cf717d020
Source dataset
uspto-grants-1985_12
Patent number
US04559177

Reaction notes

Loading…