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

HRID 2083758

반응식

HRID 2083758 반응식
[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

참가 물질

6

반응물 4

HCID 996PhenolHCID 24758Sodium hydrideHCID 71741656-Chloro-3H-isobenzofuran-1-oneHCID 178418361HCID 178418361, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매3회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-542d468f5f9c4325a7f51a97209a6155
출처 데이터셋
uspto-grants-1978_04
특허 번호
US04086350

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