Sulfuric Acid → HCID 20442878, compound

HRID 1632447Notes

Reaction equation

HRID 1632447 reaction equation
S(=O)(=O)(O)O.[CH3:6][O:7][C:8]1[C:13]([O:16][CH3:17])([O:14][CH3:15])[C:12]([O:18][CH3:19])=[CH:11][C:10](OC)([CH3:20])[CH:9]=1.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[CH3:19][O:18][C:12]1[C:13]([O:14][CH3:15])([O:16][CH3:17])[C:8]([O:7][CH3:6])=[CH:9][C:10](=[CH2:20])[CH:11]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 13188843HCID 13188843, compound

Product 1

HCID 20442878HCID 20442878, compoundYield 92.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A 6 mg quantity of concentrated sulfuric acid was added to a solution of 244 mg of 1,3,5,6,6-pentamethoxy-3-methyl-1,4-cyclohexadiene and 10 ml of chloroform. Then the mixture was stirred at room temperature for 1 hour. Thereafter the reaction mixture was neutralized by adding sodium hydrogen carbonate and filtered. The filtrate was concentrated at reduced pressure. The residue was extracted with dichloromethane, the solvent was removed at reduced pressure and the residue was concentrated, recovering 210 mg of an oily crude product. The crude product was purified by silica gel column chromatography using a 20:1 benzene-ethyl acetate mixture, giving 197 mg of 1,5,6,6-tetramethoxy-3-methylidene-1,4-cyclohexadiene in 93% of theoretical yield. The compound thus obtained was identified by NMR.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated at reduced pressure
  3. extractionThe residue was extracted with dichloromethane
  4. customthe solvent was removed at reduced pressure
  5. concentrationthe residue was concentrated
  6. customrecovering 210 mg of an oily crude product
  7. customThe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-738e4a888633486680287cfe58e3aa1a
Source dataset
uspto-grants-1984_10
Patent number
US04475992

Reaction notes

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