Acetic Acid → 5-methylpentadecanoic Acid

HRID 1937350

반응식

HRID 1937350 반응식
[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]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 241BenzeneHCID 280Carbon DioxideHCID 518964Chloroacetate

생성물 1

HCID 98599065-methylpentadecanoic Acid

시약·촉매·용매 1

HCID 23938Palladium촉매

실험 절차

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).

후처리

  1. customyielding

출처 및 근거

ORD 기록
ord-595c948599b14d7382ad08806e33c98c
출처 데이터셋
uspto-grants-2002_05
특허 번호
US06395701B1

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