Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Toluene | HCID 1140 | — |
| Reactant | alpha-Hydroxyacetophenone | HCID 68490 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Catalyst | Trifluoroacetic acid | HCID 6422 | — |
| Solvent | tert-Butyl methyl ether | HCID 15413 | — |
| Product | HCID 69714704 | HCID 69714704 | — |
Reaction Steps
The cyclic vinyl ether (2 eq.) was added to a suspension of the hydroxy-acetophenone (10 mmol) in toluene (10 ml), followed by trifluoroacetic acid (2 or 3 drops, ˜0.01 eq.). The mixture was heated at 50° C. When the reaction was complete (TLC, 2-3 hours), it was diluted with MTBE and poured into aq. NaHCO3 (sat.). The aqueous phase was separated and extracted with MTBE, and the combined organic layers were washed with brine and dried over MgSO4. The crude, obtained after evaporation of the solvents, was purified by chromatography (SiO2, EtOAc/Hexane) to afford the desired product as a colorless to pale yellow oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06939845B2 |
|---|
| Source dataset | uspto-grants-2005_09 |
|---|
| ORD ID | ord-a4b7d0094ef0486aad111d5bca936574 |
|---|
| Source note | uspto-grants-2005_09 |
|---|