Sulfuric Acid → HCID 13443700, compound

HRID 728516Notes

Reaction equation

HRID 728516 reaction equation
[CH3:1][O:2][C:3]1[C:4](=[O:10])[CH:5]=[CH:6][C:7](=[O:9])[CH:8]=1.[CH3:11][C:12]([C:14]([CH3:16])=[CH2:15])=[CH2:13].[Cr](O)(O)(=O)=O.OS(O)(=O)=O>O.C(O)(=O)C>[CH3:1][O:2][C:3]1[C:4](=[O:10])[C:5]2[C:6]([C:7](=[O:9])[CH:8]=1)=[CH:15][C:14]([CH3:16])=[C:12]([CH3:13])[CH:11]=2

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 105662,3-Dimethyl-1,3-butadieneHCID 24425Chromic AcidHCID 761462-Methoxy-1,4-benzoquinone

Product 1

HCID 13443700HCID 13443700, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
45 °C

Procedure

Methoxy-p-benzoquinone (0.50 g) and 2,3-dimethyl-1,3-butadiene (0.63 ml) were added to 23.0 mL of glacial acetic acid. The mixture was heated at 45° C. for 18.5 hrs. A chromic acid solution consisting of 1.85 g of Na2Cr2O7.2H2O, 1.16 mL water, and 0.09 mL of concentrated H2SO4 was then added, and the temperature was kept at approximately 67° C. for 1 hour. The product was precipitated by the addition of ice water, washed several times with cold water, and then dried over P2O5. A 71% yield (0.557 g) of 2-methoxy-6,7-dimethyl-1,4-naphthoquinone was obtained.

Workup

  1. additionwas then added
  2. customThe product was precipitated by the addition of ice water
  3. washwashed several times with cold water
  4. dry with materialdried over P2O5

Sources & evidence

ORD record
ord-9bbb8d065d134d7595e881c9b87f7838
Source dataset
uspto-grants-1991_09
Patent number
US05049236

Reaction notes

Loading…