Malonic Acid → 3-(4-Phenylphenyl)prop-2-enoic acid

HRID 974021

反応式

HRID 974021 の反応式
[C:1]1([C:7]2[CH:14]=[CH:13][C:10]([CH:11]=O)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(=O)[CH2:16][C:17]([OH:19])=[O:18].N1CCCCC1>N1C=CC=CC=1>[C:1]1([C:7]2[CH:14]=[CH:13][C:10]([CH:11]=[CH:16][C:17]([OH:19])=[O:18])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

5

反応物 3

HCID 867Malonic AcidHCID 8082PiperidineHCID 76689(1,1'-Biphenyl)-4-carboxaldehyde

生成物 1

HCID 254923-(4-Phenylphenyl)prop-2-enoic acid収率 76.2%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

A mixture of 4-phenylbenzaldehyde (5.17 g, 28.4 mmol), malonic acid (4.0 g), pyridine (20 ml), and piperidine (0.5 ml) was heated until gas evolution began. Heating was continued until gas evolution ceased (about 30 minutes at 90°-100° C.). The mixture was cooled, and the solid product triturated with boiling methanol (150 ml) and enough concentrated HCl to make the mixture acidic. The mixture was cooled, and the product collected by filtration, washed with water and methanol, and dried in vacuo to provide 4-phenylcinnamic acid (4.85 g, 76% yield), mp 220°-225° C. This material was dissolved in ethanol (150 ml) containing concentrated sulfuric acid (0.5 ml) and triethyl orthoacetate (3.5 ml), and refluxed for 24 hours. Removal of the solvent and recrystallization of the residue from methanol-water provided the ethyl ester (5.0 g, 92% yield), mp 88°-89° C.

後処理

  1. temperaturewas heated until gas evolution
  2. temperatureHeating
  3. custom(about 30 minutes at 90°-100° C.)
  4. temperatureThe mixture was cooled
  5. customthe solid product triturated with boiling methanol (150 ml) and enough concentrated HCl
  6. temperatureThe mixture was cooled
  7. filtrationthe product collected by filtration
  8. washwashed with water and methanol
  9. customdried in vacuo

出典と根拠

ORDレコード
ord-e3f377d3f72849ed9be058409a8f0fd8
出典データセット
uspto-grants-1991_11
特許番号
US05066658

関連ノート

読み込み中…