Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Phenylpyruvic acid | HCID 997 | — |
| Reactant | Methyl iodide | HCID 6328 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | HCID 13065771 | HCID 13065771 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 12218047 | HCID 12218047 | 59% |
Reaction Steps
A 1N aqueous solution of sodium hydroxide (20 ml, 20 mmoles) and 30 ml of dimethylformamide were added to 1.64 g (10.0 mmoles) of phenylpyruvic acid to form a solution. Then, 2.0 ml of methyl iodide was added, and the mixture was stirred at room temperature for 10 hours. The reaction mixture was acidified with 1N hydrochloric acid, and extracted with 150 ml of ether. The ether layer was dried over magnesium sulfate, and concentrated under reduced pressure to give a pale yellowish white solid. Analysis of its NMR spectrum showed that 2-oxo-3-phenylbutanoic acid formed in a yield of 59%, and 2-oxo-3-methyl-3-phenylbutanoic acid, in a yield of 21%. The NMR spectrum of the former is shown in Example 1, and that of the latter is shown in Example 73.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US05028738 |
|---|
| Source dataset | uspto-grants-1991_07 |
|---|
| ORD ID | ord-fde864653b40408685b916085e9df722 |
|---|
| Source note | uspto-grants-1991_07 |
|---|