Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | HCID 12788290 | HCID 12788290 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 12788291 | HCID 12788291 | 60% |
Reaction Steps
A mixture of 5-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-carbomethoxy-1,3-cyclohexanedione (20.8 g, 43.5 mmole), dioxane (40 ml) and 20% sodium hydroxide (40 ml) was heated at 100° C. for 2.5 hours. It was cooled in an ice bath and acidified with concentrated hydrochloric acid. This mixture was heated for one hour at 100° C., cooled to 0° C. and then neutralized with sodium bicarbonate. The resultant mixture was added to saturated sodium bicarbonate and ether. The ether extract was dried over magnesium sulfate and evaporated to an oil. Purification of this oil via column chromatography on one kg of silica gel eluted with 10% acetone-ether gave 10.9 g (60%) of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US04391827 |
|---|
| Source dataset | uspto-grants-1983_07 |
|---|
| ORD ID | ord-6e2a5f896c494935ae3a2d0e793a6ca6 |
|---|
| Source note | uspto-grants-1983_07 |
|---|