Acetone → 4-Methylheptanoic acid, (-)-

HRID 28427

反応式

HRID 28427 の反応式
[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]

参加物

6

反応物 3

HCID 180AcetoneHCID 962Water2 回HCID 15345839(6R)-2,6-Dimethylnon-2-ene

生成物 1

HCID 138003704-Methylheptanoic acid, (-)-

試薬・触媒・溶媒 2

HCID 1118Sulfuric Acid溶媒2 回HCID 57417360Sodium chloride; water溶媒

実験手順

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%].

後処理

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

出典と根拠

ORDレコード
ord-949975933a6846d19c999aa54016fa41
出典データセット
uspto-grants-2008_09
特許番号
US07419981B2

関連ノート

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