HuagongsheHuagongshe Chemistry Print Report · For research reference only
Boron trifluoride → 5-Methoxy-3-phenyl-1-tetralone
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Boron trifluoride | HCID 6356 | — |
| Reactant | 1,3-Dimethyl-2-imidazolidinone | HCID 6661 | — |
| Reactant | 2-Propenoic acid, 3-phenyl-, methyl ester | HCID 7644 | — |
| Reactant | 1,3-Propanedithiol | HCID 8013 | — |
| Reactant | 2-Methoxybenzaldehyde | HCID 8658 | — |
| Reactant | 1,2-Dithiane | HCID 136335 | — |
| Reactant | Butyllithium | HCID 178418339 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 5-Methoxy-3-phenyl-1-tetralone | HCID 12212406 | — |
Reaction Steps
o-Anisaldehyde (20.5 g) was treated with 1,3-propanedithiol (24 ml) in the presence of BF3 etherate (4 ml) and CH2Cl2 (300 ml). This dithiane derivative (4.7 g) was reacted with n-BuLi (2.5 M hexane solution) (7.3 ml), methyl cinnamate (3.4 g) and 1,3-dimethyl-2-imidazolidone-(4.6 ml) affording the desired product (M+H)+ 389. Desulfurization was accomplished with Raney Nickel and EtOH, followed by hydrolysis to the desired carboxylic acid. Cyclization to the desired 5 methoxy 3 phenyl 1 tetralone was accomplished by heating with polyphosphoric acid, (M+H)+ 253.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05128362 |
| Source dataset | uspto-grants-1992_07 |
| ORD ID | ord-db729e55edfe4cd992e0a0e5a2455b82 |
| Source note | uspto-grants-1992_07 |