HuagongsheHuagongshe Chemistry Print Report · For research reference only
Benzene → 3-(1,3-dithiolan-2-yl)-6a,7,10,10a-tetrahydro-6,6,9-trimethyl-6H-dibenzo[b,d]pyran-1-ol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Benzene | HCID 241 | — |
| Reactant | p-Toluenesulfonic acid | HCID 6101 | — |
| Reactant | trans-1-Methyl-4-(1-methylvinyl)cyclohex-2-en-1-ol | HCID 155626 | — |
| Reactant | 5-(1,3-Dithiolan-2-yl)resorcinol | HCID 11687151 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 3-(1,3-dithiolan-2-yl)-6a,7,10,10a-tetrahydro-6,6,9-trimethyl-6H-dibenzo[b,d]pyran-1-ol | HCID 21423348 | — |
Reaction Steps
In the third step of the process 5-(1,3-dithiolan-2-yl)resorcinol (V) is reacted with p-mentha-2,8-dien-1-ol having the formula ##STR10## in a suitable liquid reaction medium such as benzene or methylene chloride in the presence of an acid, such as p-toluenesulfonic acid, to induce the condensation. The procedures for this type of reaction are disclosed in Helv. Chim. Acta, 52, 1102 (1969). An elevated temperature, such as the reflux temperature, promotes the reaction and brings it to completion in less than one hour. The desired 3-(1,3-dithiolan-2-yl)-6a,7,10,10a-tetrahydro-6,6,9-trimethyl-6H-dibenzo[b,d]pyran-1-ol (VI) is then obtained from the reaction mixture, and purified, using routine operations.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04036857 |
| Source dataset | uspto-grants-1977_07 |
| ORD ID | ord-1dbbc64efd2f48caa6bbfe143df75684 |
| Source note | uspto-grants-1977_07 |