Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | tert-Butanol | HCID 6386 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | 3,5-Dimethylpyridine-2-carbonitrile | HCID 8167269 | — |
| Solvent | Acetic Acid | HCID 176 | — |
| Solvent | Sulfuric Acid | HCID 1118 | — |
| Product | HCID 18382719 | HCID 18382719 | — |
Reaction Steps
Stir a solution of 2-cyano-3,5-dimethylpyridine (20.3 g, 0.153 mol) in 100 mL of acetic acid and 20 mL of conc. sulfuric acid over 10 minutes. Add t-butanol (20 ml.) over an additional 15 minutes. Warm the solution to 75° C. and maintain for 30 minutes. Cool to room temperature and basify with 25% NaOH. Extract the product (3X) with ethyl acetate (600 mL). Combine the organic portions and wash (1X) with brine. Dry (Na2SO4), filter and concentrate in vacuo to produce the title compound as a yellowish oil (31.26 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US05104876 |
|---|
| Source dataset | uspto-grants-1992_04 |
|---|
| ORD ID | ord-80f665e243894c86a5c703c43e8bdadc |
|---|
| Source note | uspto-grants-1992_04 |
|---|
