Sulfuric Acid → 3-(1,3-Dioxaindan-5-yl)propane-1-thiol

HRID 1195289Notes

Reaction equation

HRID 1195289 reaction equation
[C:1](O)(=[S:3])[CH3:2].[O:5]1[C:16]2[C:8](=[CH:9][C:10](=[CH:14][CH:15]=2)[CH2:11]C=C)[O:7][CH2:6]1.[OH-].[Na+].S(=O)(=O)(O)O>C(O)C.O>[O:5]1[C:16]2[CH:15]=[CH:14][C:10]([CH2:11][CH2:2][CH2:1][SH:3])=[CH:9][C:8]=2[O:7][CH2:6]1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 5144SafroleHCID 14798Sodium HydroxideHCID 178418634HCID 178418634, compound

Product 1

HCID 190016193-(1,3-Dioxaindan-5-yl)propane-1-thiolYield 66.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

25 g of thioacetic acid was added to 53.5 g of safrole in portions, while stirring the mixture at a room temperature or under cooling with ice/water. The reaction was carried out for 30 minutes. A solution of 20 g of sodium hydroxide in a mixture comprising 100 ml of water and 200 ml of ethanol was added to the reaction mixture The obtained mixture was heated under reflux for 20 minutes, cooled, neutralized with dilute sulfuric acid and extracted with 1 l of benzene. The extract was washed with water and the benzene layer was dried over anhydrous sodium sulfate and purified by silica gel column chromatography (hexane) to obtain 42.8 g of the title compound as a colorless oil.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 20 minutes
  3. temperaturecooled
  4. extractionextracted with 1 l of benzene
  5. washThe extract was washed with water
  6. dry with materialthe benzene layer was dried over anhydrous sodium sulfate
  7. custompurified by silica gel column chromatography (hexane)

Sources & evidence

ORD record
ord-f908f0479d9045d1907a4d52c85a16f7
Source dataset
uspto-grants-1992_05
Patent number
US05110956

Reaction notes

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