Isopropanol → Methyl 7-octenoate

HRID 1913998

반응식

HRID 1913998 반응식
[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]

참가 물질

7

반응물 3

HCID 3776IsopropanolHCID 889477-OctenalHCID 131709961Jones' reagent

생성물 1

HCID 543921Methyl 7-octenoate수율 91%

시약·촉매·용매 3

HCID 521998p-Toluenesulfonic acid monohydrate촉매HCID 180Acetone용매HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-fc6a8588a9b2437c83f1ad1125b1f8e8
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08609886B2

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