HuagongsheHuagongshe Chemistry Print Report · For research reference only
Benzoic Acid → Methyl 4-(3-oxoprop-1-en-1-yl)benzoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Benzoic Acid | HCID 243 | — |
| Reactant | Methyl 4-Formylbenzoate | HCID 15294 | — |
| Reactant | (Triphenylphosphoranylidene)acetaldehyde | HCID 75051 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | Methyl 4-(3-oxoprop-1-en-1-yl)benzoate | HCID 53758591 | 37.9% |
Reaction Steps
A solution of 0.21 g (1.25 mmoles) of 4-carbomethoxybenzaldehyde, 0.42 g (1.25 mmoles) of formylmethylenetriphenylphosphorane and a catalytic amount of benzoic acid in 25 ml of THF was refluxed under nitrogen for 18 hours. The THF was evaporated and the recovered gum extracted repeatedly with ether. The combined ether extracts were evaporated. Flash chromatography on silica gel with 50% CH2Cl2 /hexane up to 100% CH2Cl2 gave 90 mg of a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04499299 |
| Source dataset | uspto-grants-1985_02 |
| ORD ID | ord-cc38f46755a04564876d129644065ec5 |
| Source note | uspto-grants-1985_02 |