Cyanoacetic acid → 1,3-Bis-(4-benzoyl-3-hydroxyphenoxy)-prop-2-yl cyanoacetate

HRID 621663

反応式

HRID 621663 の反応式
FC(F)(F)S(O)(=O)=O.[C:9]([C:17]1[CH:43]=[CH:42][C:20]([O:21][CH2:22][CH:23]([OH:41])[CH2:24][O:25][C:26]2[CH:31]=[CH:30][C:29]([C:32](=[O:39])[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[C:28]([OH:40])[CH:27]=2)=[CH:19][C:18]=1[OH:44])(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[C:45]([CH2:47][C:48](O)=[O:49])#[N:46]>ClCCCl>[C:45]([CH2:47][C:48]([O:41][CH:23]([CH2:22][O:21][C:20]1[CH:42]=[CH:43][C:17]([C:9](=[O:16])[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[C:18]([OH:44])[CH:19]=1)[CH2:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([C:32](=[O:39])[C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)=[C:28]([OH:40])[CH:27]=1)=[O:49])#[N:46]

参加物

5

反応物 3

HCID 9740Cyanoacetic acidHCID 62406Trifluoromethanesulfonic acidHCID 12422352,2''-Dihydroxy-4,4''-(2-hydroxy-propane-1,3-diyldioxy)dibenzophenone

生成物 1

HCID 538270821,3-Bis-(4-benzoyl-3-hydroxyphenoxy)-prop-2-yl cyanoacetate収率 87%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

3 g of trifluoromethanesulfonic acid were added to a solution of 48.5 g (0.1 mole) of 1,3-bis-(4-benzoyl-3-hydroxyphenoxy)-2-propanol and 51 g (0.6 mole) of cyanoacetic acid in 750 ml of 1,2-dichloroethane, and the solution was heated for 9 hours at a temperature of 80° to 85° C. After cooling to room temperature, the reaction mixture was washed with three times 400 ml of water. The 1,2-dichloroethane was distilled off from the reaction mixture under a pressure of 50 mbar and a temperature of 35° to 45° C. The residue remaining was recrystallized from acetonitrile. After drying, 48 g (87 percent of theory) of 1,3-bis-(4-benzoyl-3-hydroxyphenoxy)-prop-2-yl cyanoacetate were obtained in the form of slightly yellow, fine crystals having a melting point of 167° to 168° C. and a purity of 99 percent (HPLC).

後処理

  1. temperaturethe solution was heated for 9 hours at a temperature of 80° to 85° C
  2. washthe reaction mixture was washed with three times 400 ml of water
  3. distillationThe 1,2-dichloroethane was distilled off from the reaction mixture under a pressure of 50 mbar
  4. customa temperature of 35° to 45° C
  5. customThe residue remaining was recrystallized from acetonitrile
  6. customAfter drying

出典と根拠

ORDレコード
ord-bbd1c12f62974f59b1c9d937d02a0687
出典データセット
uspto-grants-1989_04
特許番号
US04824892

関連ノート

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