Acetic Acid → 5-methylpentadecanoic Acid

HRID 895324Notes

Reaction equation

HRID 895324 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-09a2f298745248bf9bddd8a1240821a6
Source dataset
uspto-grants-2005_07
Patent number
US06916777B2

Reaction notes

Loading…