Phenol → 5-Chloro-2-(phenoxymethyl)benzoic acid

HRID 2083758

反応式

HRID 2083758 の反応式
[H-].[Na+].[C:3]1([OH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[H][H].[Cl:12][C:13]1[CH:22]=[C:21]2[C:16]([CH2:17][O:18][C:19]2=[O:20])=[CH:15][CH:14]=1>CN(C)C=O>[O:9]([CH2:17][C:16]1[CH:15]=[CH:14][C:13]([Cl:12])=[CH:22][C:21]=1[C:19]([OH:20])=[O:18])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

参加物

6

反応物 4

HCID 996PhenolHCID 24758Sodium hydrideHCID 71741656-Chloro-3H-isobenzofuran-1-oneHCID 178418361HCID 178418361、化合物

生成物 1

HCID 203575185-Chloro-2-(phenoxymethyl)benzoic acid

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒3 回

実験手順

Sodium hydride (1.0 mol) is suspended in about 300 ml. of dimethylformamide and phenol (1.0 mol) in about 200 ml. of dimethylformamide is added dropwise, keeping the reaction temperature around 25° C. The mixture is stirred until hydrogen evolution is completed. 6-Chlorophthalide (1.0 mol) in about 250 ml. of dimethylformamide is then added slowly. The resulting mixture is refluxed for 2 hours and allowed to stand at room temperature overnight. The reaction mixture is diluted with ice/water and extracted several times with ether. The aqueous fraction is acidified with dilute hydrochloric acid and extracted with ether. The ether is dried and concentrated to a gummy solid which is recrystallized from a minimum volume of alcohol to give 2-phenoxymethyl-5-chlorobenzoic acid, m.p. 149°-155° C.

後処理

  1. customthe reaction temperature around 25° C
  2. temperatureThe resulting mixture is refluxed for 2 hours
  3. extractionextracted several times with ether
  4. extractionextracted with ether
  5. dry with materialThe ether is dried
  6. concentrationconcentrated to a gummy solid which
  7. customis recrystallized from a minimum volume of alcohol

出典と根拠

ORDレコード
ord-542d468f5f9c4325a7f51a97209a6155
出典データセット
uspto-grants-1978_04
特許番号
US04086350

関連ノート

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