Hydrochloric Acid → HCID 19001686, compound

HRID 486929Notes

Reaction equation

HRID 486929 reaction equation
[Sn](Cl)(Cl)(Cl)Cl.[O:6]1[C:17]2[C:9](=[CH:10][C:11](=[CH:15][CH:16]=2)[CH2:12][CH:13]=[CH2:14])[O:8][CH2:7]1.[ClH:18]>C(OCC)(=O)C>[Cl:18][CH:13]([CH3:14])[CH2:12][C:11]1[CH:15]=[CH:16][C:17]2[O:6][CH2:7][O:8][C:9]=2[CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5144SafroleHCID 24287Tin tetrachloride

Product 1

HCID 19001686HCID 19001686, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

5 g of anhydrous tin chloride was added to 100 g of safrole. Hydrochloric acid gas was passed though the mixture under cooling with ice for 1.5 hours. 2 l of ethyl acetate was added to the reaction mixture, followed by the dissolution. The obtained mixture was washed with water twice, dried over anhydrous sodium sulfate and distilled to remove the solvent. The residue was purified by silica gel column chromatography (hexane/benzene=10:1) to obtain 41.7 g of 5-(2-chloropropyl)-1,3-benzodioxole as a colorless oil. This oil was dissolved in 150 ml of ethanol, followed by the addition of 48 g of thiourea. The obtained mixture was heated under reflux for 7 days, cooled and filtered. A solution of 12.8 g of sodium hydroxide in 100 ml of water was added to the filtrate. The obtained mixture was heated under reflux for 2 hours, cooled and acidified with dilute sulfuric acid. 1 l of benzene and 1 l of water were added to the mixture to carry out the phase separation. The benzene layer was washed with water twice, dried over anhydrous sodium sulfate and distilled to remove the solvent. The residue was purified by silica gel column chromatography (hexane/benzene=10:1) to obtain 8.5 g of the title compound as a colorless oil.

Workup

  1. temperatureunder cooling with ice for 1.5 hours
  2. dissolutionfollowed by the dissolution
  3. washThe obtained mixture was washed with water twice
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationdistilled
  6. customto remove the solvent
  7. customThe residue was purified by silica gel column chromatography (hexane/benzene=10:1)

Sources & evidence

ORD record
ord-bef9f9a2d9b3453da8ffdbd866147263
Source dataset
uspto-grants-1994_03
Patent number
US05292901

Reaction notes

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