Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sulfuric Acid | HCID 1118 | — |
| Reactant | tert-Butanol | HCID 6386 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | 3,5-dimethylpyridine-2-carbonitrile | HCID 8167269 | — |
| Solvent | Acetic Acid | HCID 176 | — |
| Product | HCID 18382719 | HCID 18382719 | — |
Reaction Steps
To a stirred solution of 20.3 g (0.153 mol) of 2-cyano-3,5-dimethylpyridine in 100 mL of acetic acid was added 20 mL of conc. sulfuric acid within 10 minutes (temp. rose to 35° C.), followed by 20 mL of t-butanol over an additional 15 minutes. The solution was warmed at 75° C. for 30 minutes after which it was cooled to room temperature and basified with 25% NaOH. The product was extracted 3×with EtOAc (600 mL), which was combined and washed 1× with brine, dried (Na2SO4), filtered and concentrated in vacuo to give the title compound (31.26 g) as a yellowish oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05089496 |
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| Source dataset | uspto-grants-1992_02 |
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| ORD ID | ord-41779624e364451292f14972215b6c62 |
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| Source note | uspto-grants-1992_02 |
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