Acetic Acid → HCID 19786906、化合物

HRID 263923ノート

反応式

HRID 263923 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

HCID 19786906HCID 19786906、化合物収率 42.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-438ae82b0a104bc4beb18c92bacac370
出典データセット
uspto-grants-1997_07
特許番号
US05646149

反応ノート

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