Pentanal → HCID 86735645, compound

HRID 2083774Notes

Reaction equation

HRID 2083774 reaction equation
[CH3:1][CH:2]([CH3:18])[CH2:3]/[CH:4]=[CH:5]\[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16].[I-].[CH3:20]OC(CCCCCCCCCC[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=O.C[O-].[Na+].C(=O)CC(C)C.C(=O)CCCC>C(N(C)C)=O>[CH3:1][CH:2]([CH3:18])[CH2:3]/[CH:4]=[CH:5]\[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([O:17][CH3:20])=[O:16]

Participants

7

Reactant 5

HCID 8063PentanalHCID 115523-MethylbutanalHCID 10942334Sodium MethoxideHCID 11114590Phosphonium, (11-methoxy-11-oxoundecyl)triphenyl-, iodideHCID 86735646HCID 86735646, compound

Product 1

HCID 86735645HCID 86735645, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(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°.

Workup

  1. customto give Ph3PCH(CH2)9 --COOMe

Sources & evidence

ORD record
ord-18df89a63c4a471789cb71a3e8a36419
Source dataset
uspto-grants-1978_04
Patent number
US04086416

Reaction notes

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