HuagongsheHuagongshe Chemistry Print Report · For research reference only
Benzoic Acid → Ethyl 4-(4-bromobutyl)benzoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Benzoic Acid | HCID 243 | — |
| Reactant | Acetyl chloride | HCID 6367 | — |
| Reactant | Acetophenone | HCID 7410 | — |
| Reactant | 1-Bromo-4-phenylbutane | HCID 259668 | — |
| Reactant | Aluminum(III) Chloride | HCID 6451240 | — |
| Reactant | Sodium hypobromite | HCID 23673712 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | Ethyl 4-(4-bromobutyl)benzoate | HCID 12748303 | — |
Reaction Steps
In this case, 4-bromobutylbenzene is acylated with acetyl chloride and aluminum chloride; the resulting acetophenone is oxidized with sodium hypobromite to the benzoic acid, and this compound is esterified with ethanol and mineral acid to afford ethyl 4-(4-bromobutyl)benzoate. This ester is treated with the anion prepared from methyl methylthiomethyl sulfoxide and a strong base such as sodium hydride. The resulting dimethylmercaptal S-oxide is hydrolyzed with acid catalysis to the aldehyde intermediate XXI.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04225609 |
| Source dataset | uspto-grants-1980_09 |
| ORD ID | ord-04f7284969114f2aaacaa2468f3dce4b |
| Source note | uspto-grants-1980_09 |