HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → (6-Chloro-2-oxohexyl) triphenylphosphonium chloride
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Diazomethane | HCID 9550 | — |
| Reactant | Delta-Valerolactone | HCID 10953 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | Thionyl Chloride | HCID 24386 | — |
| Reactant | 5-Chlorovaleryl chloride | HCID 74089 | — |
| Reactant | 1,6-Dichlorohexan-2-one | HCID 12806018 | — |
| Reactant | Diazomethyl ketone | HCID 54572627 | — |
| Catalyst | Zincchloride | HCID 3007855 | — |
| Product | (6-Chloro-2-oxohexyl) triphenylphosphonium chloride | HCID 20526427 | — |
Reaction Steps
The latter reactions are exemplified by the cleavage of δ-valerolactone with zinc chloride and thionyl chloride to produce 5-chlorovaleryl chloride, reaction of that acid chloride with diazomethane, followed by treatment of the resulting diazomethylketone with hydrochloric acid to yield 1,6-dichloro-2-hexanone, and reaction of that ketone with triphenylphosphine to afford (6-chloro-2-oxohexyl) triphenylphosphonium chloride. This product is converted to (5-chloropentanoylmethylene)triphenyl phosphorane by reaction with aqueous sodium hydroxide.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04075407 |
| Source dataset | uspto-grants-1978_02 |
| ORD ID | ord-2b9f4fcf538b4013b53e3f48c4cc2ab1 |
| Source note | uspto-grants-1978_02 |