Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sulfuric Acid | HCID 1118 | — |
| Reactant | Sodium Azide | HCID 33557 | — |
| Reactant | 5-methoxy-3,3-dimethyl-1-indanone | HCID 12283214 | — |
| Solvent | Benzene | HCID 241 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 12283221 | HCID 12283221 | 98% |
Reaction Steps
A solution of 5-methoxy-3,3-dimethyl-indane-1-one (Intermediate 16, 3.3 g, 17.4 mmol) in benzene (50 mL) was treated with concentrated sulfuric acid (10 mL) and heated to 60° C. Sodium azide (1.95 g, 30 mmol) was added in small portions and after the addition was complete, the reaction mixture was heated further for 4 h. It was then cooled, diluted with water and extracted with chloroform (×3). The combined organic phase was dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to afford the title compound as a brown solid (3.5 g, quantitative by weight).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06252090B1 |
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| Source dataset | uspto-grants-2001_06 |
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| ORD ID | ord-8b323cb3ee444b89afb81cf1b0fed361 |
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| Source note | uspto-grants-2001_06 |
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