Pyridine → 12-(Acryloyloxy)dodecanoic acid

HRID 1734970노트

반응식

HRID 1734970 반응식
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14].N1C=CC=CC=1.[C:22](Cl)(=[O:25])[CH:23]=[CH2:24]>O1CCCC1>[C:22]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])(=[O:25])[CH:23]=[CH2:24]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 13140Acryloyl chlorideHCID 7903412-Hydroxydodecanoic Acid

생성물 1

HCID 2232822312-(Acryloyloxy)dodecanoic acid수율 40.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

12-Hydroxydodecanoic acid (5.0 g, 0.023 mol) dissolved in tetrahydrofuran (100 ml) and pyridine (2.16 g, 0,027 mol) was cooled to 0° C. Acryloyl chloride (3.15 g, 0.023 mol) in tetrahydrofuran (75 ml) was then added dropwise to the solution. The mixture was stirred for 5 hours at 0° C. then stirred overnight at room temperature. The precipitated pyridinium salt was filtered off and the solvent removed under vacuum. The resulting liquid was purified by flash chromatography (silica gel/chloroform) to give 2.5 g (40%) of the title compound. 1H NMR (60 MHz, CDCl3): δ1.20 (s, 18H, CH2), 2.15 (m, 2H, CH2COOH), 4.0 (m, 2H, COOCH2), 5.7-6.0 (m, 3H, CH2 =and =CH).

후처리

  1. stirringthen stirred overnight at room temperature
  2. filtrationThe precipitated pyridinium salt was filtered off
  3. customthe solvent removed under vacuum
  4. customThe resulting liquid was purified by flash chromatography (silica gel/chloroform)

출처 및 근거

ORD 기록
ord-bff71cdb8d7a4b18bc2f3eec85f2dc55
출처 데이터셋
uspto-grants-1996_07
특허 번호
US05536490

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