HuagongsheHuagongshe Chemistry Print Report · For research reference only
Octanoic Acid → 4-Cyanobenzaldehyde
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Octanoic Acid | HCID 379 | — |
| Reactant | Dicyclohexylcarbodiimide | HCID 10868 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | (4-(1,3-dioxolan-2-yl)phenyl)methanamine | HCID 10559254 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 4-Cyanobenzaldehyde | HCID 66042 | 40% |
Reaction Steps
The 4-(1,3-dioxacyclopent-2-yl)benzylamine is condensed with octanoic acid in dichloromethane in the presence of a peptide coupling system consisting of DCC and HOBt according to a method already described (Ouari O.; Polidori A.; Pucci B.; Tordo P.: Chalier F. J. Org. Chem. 1999, 64, 3554-3556) and then the dioxolane protecting group is removed by treatment in a 1:1, v/v, acetic acid/water mixture. Compound 3 is subsequently purified by silica gel chromatography (eluent: cyclohexane/EtOAc, 6:4, v/v) to give a white powder with a yield of 40% from the 4-cyanobenzaldehyde.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08173843B2 |
| Source dataset | uspto-grants-2012_05 |
| ORD ID | ord-06567bf4ccce44dfa8543fe72c56cd12 |
| Source note | uspto-grants-2012_05 |