Isopropanol → Methyl 7-octenoate

HRID 1913998

反応式

HRID 1913998 の反応式
[CH:1](=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]=[CH2:8].C[C:11](C)=[O:12].OS(O)(=O)=O.O=[Cr](=O)=O.C(O)(C)C>CC(C)=O.CO.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[C:1]([O:12][CH3:11])(=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]=[CH2:8]

参加物

7

反応物 3

HCID 3776IsopropanolHCID 889477-OctenalHCID 131709961Jones' reagent

生成物 1

HCID 543921Methyl 7-octenoate収率 91%

試薬・触媒・溶媒 3

HCID 521998p-Toluenesulfonic acid monohydrate触媒HCID 180Acetone溶媒HCID 887Methanol溶媒

実験手順

Crude 7-octenal (30.5 g) (90.0% in gas chromatography simple area %, net: 27.5 g, 0.22 mol; cis-6-octenal: 4.7% in gas chromatography simple area %, and trans-6-octenal: 4.5% in gas chromatography simple area %) was dissolved in 95% by mass acetone aqueous solution (300.0 g). After adding Jones reagent (3M chromic acid-sulfuric acid aqueous solution) (100.0 mL) and stirring at room temperature for 2 hours, isopropanol (20.0 g) was added thereto. After the precipitate was filtered off and acetone was distilled off from the filtrate, the filtrate was extracted with ethyl acetate. After the ethyl acetate layer was washed with water and saturated sodium chloride solution, the solvent was distilled off to obtain a crude product. Subsequently, this product was dissolved in methanol (300.0 g). After adding p-toluenesulfonic acid mono hydrate (3.0 g) thereto, the solution was heated at 60° C. for 2 hours. The solution was extracted with ethyl acetate, and the organic layer was washed with water and sodium carbonate aqueous solution. After that, the organic layer obtained by distilling off the solvent was distilled under a reduced pressure of 500 Pa. With this procedure, crude methyl 7-octenoate (34.3 g) (90.0% in gas chromatography simple area %, net: 30.9 g, net: 0.20 mol, yield: 91%; cis-6-octenonitrile: 4.7% in gas chromatography simple area %, and trans-6-octenonitrile: 4.5% in gas chromatography simple area %) was obtained as a distillate.

後処理

  1. filtrationAfter the precipitate was filtered off
  2. distillationacetone was distilled off from the filtrate
  3. extractionthe filtrate was extracted with ethyl acetate
  4. washAfter the ethyl acetate layer was washed with water and saturated sodium chloride solution
  5. distillationthe solvent was distilled off
  6. customto obtain a crude product
  7. temperaturethe solution was heated at 60° C. for 2 hours
  8. extractionThe solution was extracted with ethyl acetate
  9. washthe organic layer was washed with water and sodium carbonate aqueous solution
  10. customAfter that, the organic layer obtained
  11. distillationby distilling off the solvent
  12. distillationwas distilled under a reduced pressure of 500 Pa

出典と根拠

ORDレコード
ord-fc6a8588a9b2437c83f1ad1125b1f8e8
出典データセット
uspto-grants-2013_12
特許番号
US08609886B2

関連ノート

読み込み中…