HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-Methoxybenzyl alcohol → 5-Hydroxy-4-(4-methoxybenzyloxy)-2,6,6-trimethyl-2-cyclohepten-1-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-Methoxybenzyl alcohol | HCID 7738 | — |
| Reactant | 3,6,6-Trimethyl-8-oxabicyclo[5.1.0]oct-2-en-4-one | HCID 557706 | — |
| Catalyst | p-Toluenesulfonic acid | HCID 6101 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 5-Hydroxy-4-(4-methoxybenzyloxy)-2,6,6-trimethyl-2-cyclohepten-1-one | HCID 22922331 | 51% |
Reaction Steps
To a solution of eucarvone-4,5-oxide, i.e. 4,5-epoxy-2,6,6-trimethyl-2-cyclohepten-1-one (50 g, 0.3M), in tetrahydrofuran (150 ml), 4-methoxybenzyl alcohol (55 g, 0.4M) and p-toluenesulfonic acid (2 g) were added, and it was heated under reflux for eight hours, concentrated, and then purified by silica gel column chromatography using hexane-ethyl acetate (10:1) as an eluent to obtain 46.7 g (50%) of 5-hydroxy-4-(4-methoxybenzyloxy)-2,6,6-trimethyl-2-cyclohepten-1-one (AUM09) as a light yellow oily product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05661166 |
| Source dataset | uspto-grants-1997_08 |
| ORD ID | ord-4909384c81e6492398071a54f16d1227 |
| Source note | uspto-grants-1997_08 |