Tributylamine → 1,20-Eicosanediol

HRID 895300

반응식

HRID 895300 반응식
[CH2:1]([OH:22])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][OH:21].C(N(CCCC)CCCC)CCC.C1(C)C(S(NN)(=O)=O)=CC=CC=1>>[CH2:20]([OH:21])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][OH:22]

참가 물질

4

반응물 3

HCID 7622TributylamineHCID 11499339STK331035HCID 54323900HCID 54323900, 화합물2회

생성물 1

HCID 41346901,20-Eicosanediol

실험 절차

Hydrogenation of 10-eicosene-1,20-diol: Two hundred fifty grams of the 10-eicosene-1,20-diol were placed in a twelve liter flask outfitted with a heating mantle, mechanical stirrer, condenser, and nitrogen inlet. Three liters of xylenes were added. Two equivalents each tributylamine and toluenesulfonhydrazide were added. Stirring and nitrogen flow were initiated and the solution slowly heated until the reaction was at reflux. The reaction was refluxed overnight, and then cooled to room temperature. The product, 1,20-eicosanediol, precipitated from solution and was filtered, washing with methanol. The crude product was recrystallized once from methanol, yielding white crystals with a melting point of about 101° C. The product was 99% pure by gas chromatography. IR(KBr): 3419, 3357, 2919, 2848, 1469, 1355, 1321, 1124, 1055, 1034, 999, 969, 722, 610, 502 cm−1; 1H NMR(300 MHz, toluene-d8, elevated temperature): * 3.3 (t, 4H), 1.3 (bd, 36H), 0.5 (m, 2H).

후처리

  1. temperaturethe solution slowly heated until the reaction
  2. temperatureat reflux
  3. temperatureThe reaction was refluxed overnight
  4. customThe product, 1,20-eicosanediol, precipitated from solution
  5. filtrationwas filtered
  6. washwashing with methanol
  7. customThe crude product was recrystallized once from methanol
  8. customyielding white crystals with a melting point of about 101° C

출처 및 근거

ORD 기록
ord-9171ce29edd14af0befab110b543a04c
출처 데이터셋
uspto-grants-2005_07
특허 번호
US06915168B1

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