Phenol → 4-Phenoxy-4'-phenylethynylbenzophenone

HRID 22100

反応式

HRID 22100 の反応式
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.F[C:9]1[CH:30]=[CH:29][C:12]([C:13]([C:15]2[CH:20]=[CH:19][C:18]([C:21]#[C:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:17][CH:16]=2)=[O:14])=[CH:11][CH:10]=1.C1(C)C=CC=CC=1>CC(N(C)C)=O>[O:7]([C:9]1[CH:30]=[CH:29][C:12]([C:13]([C:15]2[CH:20]=[CH:19][C:18]([C:21]#[C:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:17][CH:16]=2)=[O:14])=[CH:11][CH:10]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

5

反応物 3

HCID 996PhenolHCID 1140TolueneHCID 40956574-Fluoro-4'-(phenylethynyl)benzophenone

生成物 1

HCID 193892734-Phenoxy-4'-phenylethynylbenzophenone収率 96.3%

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

反応条件

温度
23 °C

実験手順

A 100 mL flask equipped with nitrogen inlet, overhead stirring assembly, Dean-Stark trap, and reflux condenser was charged with phenol (0.35 g, 0.0038 mol), 4-fluoro-4'-phenylethynylbenzophenone (0.10 g, 0.0038 mol) potassium carbonate (0.39 g, 0.003 mol), 25 mL of toluene, and 50 mL of DMAc. The mixture was heated to reflux and water was removed by azeotropic distillation, followed by the removal of toluene over a 20 hour period. The reaction was cooled to 23° C., and the mixture was poured into 1 L of acidic (HCl) water. The precipitate was collected by filtration to afford 1.37 g (96%) of 4-phenoxy-4'-phenylethynylbenzophenone as a white powder: mp 165.5° C. IR (KBr): 2216 cm-1 (ethynyl), 1650 cm-1 (carbonyl): 1H-NMR (CDCl3): 7.8-6.8 pp, (m H aromatic). Anal Calcd. for C27H18O2 : %C=86.61, %H=4.85. Found: %C=86.46, %H=4.68. The structure of this compound is given below: ##STR10## The DSC thermogram of this compound is presented in FIG. 3.

後処理

  1. customA 100 mL flask equipped with nitrogen inlet
  2. temperatureDean-Stark trap, and reflux condenser
  3. temperatureThe mixture was heated
  4. temperatureto reflux
  5. customwater was removed by azeotropic distillation
  6. customfollowed by the removal of toluene over a 20 hour period
  7. additionthe mixture was poured into 1 L of acidic (HCl) water
  8. filtrationThe precipitate was collected by filtration

出典と根拠

ORDレコード
ord-8d97f50bb18c49e68e56ab46f56670b8
出典データセット
uspto-grants-1995_06
特許番号
US05426234

関連ノート

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