Sulfuric Acid → 4-n-Octyloxy-1-naphthol

HRID 904713

반응식

HRID 904713 반응식
[CH:1]1[CH:6]=[C:5]2[C:7]([OH:12])=[CH:8][CH:9]=[C:10]([OH:11])[C:4]2=[CH:3][CH:2]=1.S(=O)(=O)(O)O>C(O)CCCCCCC>[CH2:5]([O:12][C:7]1[C:5]2[C:4](=[CH:3][CH:2]=[CH:1][CH:6]=2)[C:10]([OH:11])=[CH:9][CH:8]=1)[CH2:6][CH2:1][CH2:2][CH2:3][CH2:4][CH2:10][CH3:9]

참가 물질

4

반응물 2

HCID 1118Sulfuric AcidHCID 113051,4-Naphthalenediol

생성물 1

HCID 150823944-n-Octyloxy-1-naphthol수율 103.5%

시약·촉매·용매 1

HCID 9571-Octanol용매

반응 조건

온도
50 °C

실험 절차

216 g of naphthohydroquinone and 527 g of n-octyl alcohol were placed in a 2 l three-necked flask, and 114 ml of concentrated sulfuric acid was dropwisely added thereto for 30 minutes under nitrogen gas stream while stirring. Thereafter, the reaction mixture was heated at 50° C. for 1 hour and then cooled to room temperature. The reaction mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with ammonia-water until the washing reached pH of 5 to 6. The ethyl acetate layer was further washed two times with an aqueous sodium chloride solution and, then, dried with anhydrous sodium sulfate. The dried ethyl acetate solution was concentrated under reduced pressure to precipitate crystals. The crystals were filtered off, and the filtrate was further concentrated under reduced pressure to distill off ethyl acetate and n-octyl alcohol to obtain oily substance. The oily substance was purified by column chromatography using a mixed solvent of n-hexane and ethyl acetate and, then, recrystallized from n-hexane to obtain 190 g of white crystals having a melting point of 73° to 74° C.

후처리

  1. temperaturecooled to room temperature
  2. extractionThe reaction mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with ammonia-water until the washing
  4. washThe ethyl acetate layer was further washed two times with an aqueous sodium chloride solution
  5. dry with materialdried with anhydrous sodium sulfate
  6. concentrationThe dried ethyl acetate solution was concentrated under reduced pressure
  7. customto precipitate crystals
  8. filtrationThe crystals were filtered off
  9. concentrationthe filtrate was further concentrated under reduced pressure
  10. distillationto distill off ethyl acetate and n-octyl alcohol
  11. customto obtain oily substance
  12. customThe oily substance was purified by column chromatography
  13. customrecrystallized from n-hexane

출처 및 근거

ORD 기록
ord-9913a14bddcc48beb48e65a7b88fb126
출처 데이터셋
uspto-grants-1983_12
특허 번호
US04419439

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