Acetic Acid → 5-methylpentadecanoic Acid

HRID 2180927

Reaction equation

HRID 2180927 reaction equation
[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]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 241BenzeneHCID 280Carbon DioxideHCID 518964Chloroacetate

Product 1

HCID 98599065-methylpentadecanoic Acid

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

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).

Workup

  1. customyielding

Sources & evidence

ORD record
ord-5193fe71245b4624962dd762a5859225
Source dataset
uspto-grants-2005_05
Patent number
US06890894B2

Linked notes

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