HuagongsheHuagongshe Chemistry Print Report · For research reference only
Bromide ion → 2-Allylphenol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Bromide ion | HCID 259 | — |
| Reactant | Phenol | HCID 996 | — |
| Reactant | Diethyl Ether | HCID 3283 | — |
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Product | 2-Allylphenol | HCID 15624 | — |
Reaction Steps
Phenol 25 may be treated with NaH in DMF and then alkylated with an allylic bromide to give ether 30. Claisen rearrangement of 30 under thermal conditions gives ortho-allyl phenol 31. Oxidation of the double bond in 31 with OsO4/NMO followed by cleavage with NaIO4 provides the lactol 32. Jones oxidation then provides lactone 33.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06222048B1 |
| Source dataset | uspto-grants-2001_04 |
| ORD ID | ord-b7d538998ef745339debbef27317b340 |
| Source note | uspto-grants-2001_04 |