Acetone → 4-Methylheptanoic acid, (-)-

HRID 28427

반응식

HRID 28427 반응식
[CH3:1][C:2](=[CH:4][CH2:5][CH2:6][C@H](C)CCC)[CH3:3].[OH2:12].C[C:14]([CH3:16])=[O:15]>OS(O)(=O)=O.[Cl-].[Na+].O>[CH3:1][C@H:2]([CH2:4][CH2:5][CH3:6])[CH2:3][CH2:16][C:14]([OH:12])=[O:15]

참가 물질

6

반응물 3

HCID 180AcetoneHCID 962Water2회HCID 15345839(6R)-2,6-Dimethylnon-2-ene

생성물 1

HCID 138003704-Methylheptanoic acid, (-)-

시약·촉매·용매 2

HCID 1118Sulfuric Acid용매2회HCID 57417360Sodium chloride; water용매

실험 절차

To (R)-2,6-dimethyl-non-2-ene (20 g, 0.13 mol) in acetone (433 mL) was added a solution of CrO3 (39 g, 0.39 mol) in H2SO4 (33 mL)/H2O (146 mL) over 50 minutes. After 6 hours a further amount of CrO3 (26 g, 0.26 mol) in H2SO4 (22 mL)/H2O (100 mL) was added. After 12 hours the solution was diluted with brine and the solution extracted with ether. The combined organic phases were dried (MgSO4) and concentrated. Flash chromatography (gradient of 6:1 to 2:1 hexane/EtOAc) gave (R)-4-methyl-heptanoic acid as an oil. 12.1 g; 65%. MS, m/z (relative intensity): 143 [M−H, 100%].

후처리

  1. extractionthe solution extracted with ether
  2. dry with materialThe combined organic phases were dried (MgSO4)
  3. concentrationconcentrated

출처 및 근거

ORD 기록
ord-949975933a6846d19c999aa54016fa41
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07419981B2

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