Acetic Acid → 5-methylpentadecanoic Acid

HRID 394463

Reaktionsgleichung

Reaktionsgleichung von HRID 394463
[C:1](O)(=O)[CH3:2].Cl[CH2:6][C:7]([O-])=O.[C:10](=[O:12])=[O:11].[CH:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>[Pd]>[CH3:15][CH:14]([CH2:13][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:6][CH2:7][CH2:1][CH3:2])[CH2:13][CH2:18][CH2:17][C:10]([OH:12])=[O:11]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 241BenzeneHCID 280Carbon DioxideHCID 518964Chloroacetate

Produkt 1

HCID 98599065-methylpentadecanoic Acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23938PalladiumKatalysator

Versuchsvorschrift

See GENERAL PROCEDURE I. Decyl bromide (compound (1), R═CH3(CH2)9—) is converted to its Grignard reagent with magnesium in dry ether (I, Step (a)). To this is added 5-chloro-2-pentanone (Aldrich C6,2660-3) (I, Step (b)). The reaction mixture is worked up with acetic anhydride (I, Step (c)) to form chloroacetate (3). Acetic acid is eliminated by refluxing (3) in a suitable solvent, e.g., benzene (I, Step (d)) yielding a mixture of chloro-olefin isomers (4). (4) is converted to its Grignard reagent following standard practice. (I, Step (e)). The Grignard reagent is treated with carbon dioxide and aqueous acidic workup (I, Step (f)) followed by catalytic hydrogenation (Pd catalyst) to form 5-methylpentadecanoic acid, (5).

Aufarbeitung

  1. customyielding

Quellen und Nachweise

ORD-Eintrag
ord-6aff7fa8124c4d47b3b6e9c9f07872ea
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06602845B2

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