Methanol → 5-Methyl-2-(prop-1-en-2-yl)hex-4-enoic acid

HRID 2273834ノート

反応式

HRID 2273834 の反応式
[C:1]([O:7]C(C)(C=C)C)(=[O:6])[CH:2]=[C:3]([CH3:5])[CH3:4].CO>O>[C:3]([CH:2]([CH2:1][CH:2]=[C:3]([CH3:5])[CH3:4])[C:1]([OH:7])=[O:6])([CH3:4])=[CH2:5]

参加物

4

反応物 2

HCID 887MethanolHCID 106786982-Methyl-3-buten-2-yl senecioate

生成物 1

HCID 30138945-Methyl-2-(prop-1-en-2-yl)hex-4-enoic acid収率 200%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

In a nitrogen atmosphere, a mixture of the 125 mmol of sodium hydride, obtained from 5.00 g of a 60% suspension in mineral oil by removal of mineral oil with n-hexane washing, and 30 ml of toluene was heated to reflux with stirring, and subjected to dropwise addition of 20.0 g of 2-methyl-3-buten-2-yl senecioate having a purity of 96.9% over one hour. After reflux was continued for 22 hours, the reaction mixture was cooled to room temperature, and 10 ml of methanol and 40 ml of water were added dropwise thereto. The organic phase was extracted with water and then discarded. The aqueous phases were combined and then made acidic with 20% hydrochloric acid, followed by extraction with diethyl ether. The diethyl ether solution was subjected to typical work-up including washing, drying and concentration to obtain 20.0 g of the crude product having a purity of 3.6% on basis of stoichiometric amount. The content of each isomer in the crude product was analyzed using capillary GC analysis and GC-MS under the similar conditions as in Example 1. The results are shown in Table 2.

後処理

  1. temperaturewas heated
  2. temperatureto reflux
  3. temperatureAfter reflux
  4. extractionThe organic phase was extracted with water
  5. extractionfollowed by extraction with diethyl ether
  6. washincluding washing
  7. customdrying
  8. concentrationconcentration

出典と根拠

ORDレコード
ord-0d5075b227224b59be75c847d7913878
出典データセット
uspto-grants-2015_09
特許番号
US09126923B2

反応ノート

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