Acetic Acid → 5-methylpentadecanoic Acid

HRID 1937350Notes

Reaction equation

HRID 1937350 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-595c948599b14d7382ad08806e33c98c
Source dataset
uspto-grants-2002_05
Patent number
US06395701B1

Reaction notes

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