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Acetone → 4-Methylheptanoic acid, (-)-
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Acetone | HCID 180 | — |
| 反応物 | Water | HCID 962 | — |
| 反応物 | (6R)-2,6-Dimethylnon-2-ene | HCID 15345839 | — |
| 溶媒 | Sulfuric Acid | HCID 1118 | — |
| 溶媒 | Sodium chloride; water | HCID 57417360 | — |
| 生成物 | 4-Methylheptanoic acid, (-)- | HCID 13800370 | — |
反応手順
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%].
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US07419981B2 |
| 出典データセット | uspto-grants-2008_09 |
| ORD ID | ord-949975933a6846d19c999aa54016fa41 |
| 出典メモ | uspto-grants-2008_09 |