Sulfuric Acid → HCID 13592062, compound

HRID 2351006Notes

Reaction equation

HRID 2351006 reaction equation
[CH2:1]([CH:4]1[S:8][C:7]2[C:9]([CH3:19])=[C:10]([O:15]COC)[C:11]([CH3:14])=[C:12]([CH3:13])[C:6]=2[O:5]1)[CH:2]=[CH2:3].S(=O)(=O)(O)O>C(O)(=O)C>[CH2:1]([CH:4]1[S:8][C:7]2[C:9]([CH3:19])=[C:10]([OH:15])[C:11]([CH3:14])=[C:12]([CH3:13])[C:6]=2[O:5]1)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 14802196HCID 14802196, compound

Product 1

HCID 13592062HCID 13592062, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

0.9 g of 2-allyl-5-methoxymethoxy-4,6,7-trimethyl-1,3-benzoxathiole (prepared as described in Example 89) was dissolved in 8 ml of acetic acid, and 3 drops of 10% v/v aqueous sulfuric acid were added to the resulting solution, which was then heated at 50° C. for 30 minutes. The solution was then cooled down to room temperature, and the reaction mixture was condensed by evaporation under reduced pressure. The condensate was dissolved in benzene, and the solution was washed with water and then dried over anhydrous sodium sulfate. The benzene was distilled off, and the resulting crude product was purified by silica gel Lobar column chromatography. The title compound, melting at 78.5°-79.5° C., was obtained from the fraction eluted with benzene.

Workup

  1. temperatureThe solution was then cooled down to room temperature
  2. customcondensed
  3. customby evaporation under reduced pressure
  4. dissolutionThe condensate was dissolved in benzene
  5. washthe solution was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe benzene was distilled off
  8. customthe resulting crude product was purified by silica gel Lobar column chromatography

Sources & evidence

ORD record
ord-05d17f1b970b434bbd45af734d030646
Source dataset
uspto-grants-1989_10
Patent number
US04871762

Reaction notes

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