Acetic Acid → HCID 19786906, 화합물

HRID 263923노트

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HRID 263923 반응식
[C:1](O)(=O)[CH2:2][C:3]([OH:5])=[O:4].[C:8]([C:12]1[CH:13]=[C:14]([CH:17]=[C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:19]=1[OH:20])C=O)([CH3:11])([CH3:10])[CH3:9].N1CCCCC1.C(O)(=O)C>C1(C)C=CC=CC=1.O>[CH3:11][C:8]([C:12]1[CH:13]=[C:14]([C:2](=[CH2:1])[C:3]([OH:5])=[O:4])[CH:17]=[C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:19]=1[OH:20])([CH3:9])[CH3:10]

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 867Malonic AcidHCID 8082PiperidineHCID 732193,5-Di-tert-butyl-4-hydroxybenzaldehyde

생성물 1

HCID 19786906HCID 19786906, 화합물수율 42.1%

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매

실험 절차

A solution of malonic acid (Aldrich, 4.36 g, 41.9 mmol), 3,5-di-tert-butyl-4-hydroxybenzaldehyde (Aldrich, 5.00 g, 20.9 mmol), piperidine (Aldrich, 0.18 g, 2.10 mmol) and acetic acid (0.13 g, 2.10 mmol) in toluene (100 mL) was warmed at reflux (water removed using a Dean-Stark trap). After 5.5 h malonic acid was added (4.36 g, 41.9 mmol) and the reaction mixture was warmed at reflux for 12 h. The reaction mixture was cooled to ambient temperature and concentrated in vacuo. The residue was chromatographed (SiO2, flash, methanol-methylene chloride, 5:95) to give 2.43 g (42.1% yield of (E)-1-(3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl propenoic acid as a white solid.

후처리

  1. customremoved
  2. additionAfter 5.5 h malonic acid was added (4.36 g, 41.9 mmol)
  3. temperaturethe reaction mixture was warmed
  4. temperatureat reflux for 12 h
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed (SiO2, flash, methanol-methylene chloride, 5:95)

출처 및 근거

ORD 기록
ord-438ae82b0a104bc4beb18c92bacac370
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05646149

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