HuagongsheHuagongshe Chemistry Print Report · For research reference only
Pentanal → HCID 86735645, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Pentanal | HCID 8063 | — |
| Reactant | 3-Methylbutanal | HCID 11552 | — |
| Reactant | Sodium Methoxide | HCID 10942334 | — |
| Reactant | Phosphonium, (11-methoxy-11-oxoundecyl)triphenyl-, iodide | HCID 11114590 | — |
| Reactant | HCID 86735646 | HCID 86735646 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 86735645 | HCID 86735645 | 83% |
Reaction Steps
(Z)-14-Methyl-11-pentadecenoic acid. 10-(Methoxycarbonyl)-decyltriphenylphosphonium iodide having a melting point of 126°-129° (N. Petragnani and G. Schill, Chem. Ber., 97, 3293, (1964)), was treated with NaOMe and HCONMe2 to give Ph3PCH(CH2)9 --COOMe. It was then treated with isovaleraldehyde ((CH3)2CHCH2CH=O)(as with valeraldehyde in the Pentragnani et al. process) to give methyl (Z)-14-methyl-11-pentadecenate (83% yield) as a yellow oil; PMR (CDCl3) δ 5.44 m (CH=CH), 3.70s (COOCH3), 0.90d (Me2C, J = 6.0 Hz). The ester, without distillation, still contained 5% triphenylphosphine oxide. Saponification afforded 78% of (Z)-14-methyl-11-pentadecenoic acid, free of Ph3PO. A sample was distilled, bp 134°-136° (0.003 mm), mp 12.5°.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04086416 |
| Source dataset | uspto-grants-1978_04 |
| ORD ID | ord-18df89a63c4a471789cb71a3e8a36419 |
| Source note | uspto-grants-1978_04 |