HuagongsheHuagongshe Chemistry Print Report · For research reference only
2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 5-Hydroxy-6-methoxy-3,4-dihydronaphthalen-1(2H)-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone | HCID 6775 | — |
| Reactant | 1-Tetralone | HCID 10724 | — |
| Reactant | HCID 22244790 | HCID 22244790 | — |
| Solvent | 1,4-Dioxane--water (1/1) | HCID 21886435 | — |
| Product | 5-Hydroxy-6-methoxy-3,4-dihydronaphthalen-1(2H)-one | HCID 21862723 | — |
Reaction Steps
The 5-hydroxy isomer 7 was converted to 5-acetoxy-6-methoxy-1,2,3,4-tetrahydronaphthalene (9) in 95% yield. Reaction of the 9 with DDQ in dioxane-water led to the formation of tetralone 10 as a single isomer in 96% yield. The correct position of the keto group was confirmed by single-crystal X-ray crystallography. The acetate was removed by treating tetralone 10 with sodium bicarbonate in methanol to form 5-hydroxy-6-methoxy-1-tetralone (11).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07001926B2 |
| Source dataset | uspto-grants-2006_02 |
| ORD ID | ord-7a6c079709344db7a039290a4e90fa34 |
| Source note | uspto-grants-2006_02 |