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4-Coumaric acid → Hexadecyl 3-(4-hydroxyphenyl)prop-2-enoate

HRID 896724
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HRID 896724 반응식
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6]=[CH:7][C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1.[CH2:13](O)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>O>[CH2:28]([O:9][C:8](=[O:10])[CH:7]=[CH:6][C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[CH:12][CH:11]=1)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH3:13]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 3224-Coumaric acidHCID 1140TolueneHCID 2682Cetyl AlcoholHCID 6101p-Toluenesulfonic acid

생성물 1

HCID 54379095Hexadecyl 3-(4-hydroxyphenyl)prop-2-enoate수율 21.3%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

4-Hydroxy cinnamic acid (10 g, 61 mmol) was combined with 1-hexadecanol (14.0 g, 58 mmol), p-toluenesulfonic acid (1.2 g, 6.3 mmol) and 100 ml toluene and heated to 140° C. for 24 h with continual removal of water using a Dean-Stark distillation apparatus. The mixture was cooled to room temperature and 50 ml ethyl acetate added. The solution was washed with water, 5% sodium hydrogen carbonate, brine and then dried over magnesium sulfate. The product was recrystallized from ethyl acetate to give 4.8 g 3-(4-hydroxy-phenyl)-acrylic acid hexadecyl ester.

후처리

  1. distillationa Dean-Stark distillation apparatus
  2. addition50 ml ethyl acetate added
  3. washThe solution was washed with water, 5% sodium hydrogen carbonate, brine
  4. dry with materialdried over magnesium sulfate
  5. customThe product was recrystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-c67a929284f64ecaa94266ffdd20d7f4
출처 데이터셋
uspto-grants-2005_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06919404B2

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