Acetic Acid → 5-methylpentadecanoic Acid

HRID 895324ノート

反応式

HRID 895324 の反応式
[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]

参加物

6

反応物 4

HCID 176Acetic AcidHCID 241BenzeneHCID 280Carbon DioxideHCID 518964Chloroacetate

生成物 1

HCID 98599065-methylpentadecanoic Acid

試薬・触媒・溶媒 1

HCID 23938Palladium触媒

実験手順

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).

後処理

  1. customyielding

出典と根拠

ORDレコード
ord-09a2f298745248bf9bddd8a1240821a6
出典データセット
uspto-grants-2005_07
特許番号
US06916777B2

反応ノート

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