4-Chlorophenol → 2-(2-(4-Chlorophenoxy)phenyl)acetic acid

HRID 1625162노트

반응식

HRID 1625162 반응식
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=[O:10].[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+]>CC1C=CC=CC=1C.[Cu]>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[CH2:8][C:9]([OH:11])=[O:10])=[CH:15][CH:14]=1

참가 물질

6

반응물 3

HCID 46844-ChlorophenolHCID 11430Potassium CarbonateHCID 17124o-Chlorophenylacetic acid

생성물 1

HCID 122458712-(2-(4-Chlorophenoxy)phenyl)acetic acid

시약·촉매·용매 2

HCID 23978Copper촉매HCID 7237O-Xylene용매

반응 조건

온도
27.5 °C

실험 절차

To a solution of o-chlorophenylacetic acid (330 g) in o-xylene (4000 mL) is added 4-chlorophenol (306 g), K2CO3 (354 g), and copper powder (18 g) at 25-30° C. The mixture is heated at reflux for 2-3 hours and water is removed by azeotropic distillation. The reaction mixture is maintained for 1-2 hours at 25-30° C. and water (4000 mL) is added. Organic and aqueous layers are separated and the organic layer is washed with water (4000 mL). The pH of combined aqueous layers is adjusted to 1-1.5 by addition of aqueous HCl (100 mL) at 0-5° C. The formed solid is collected by filtration, washed with water (3000 mL) and hexane (500 mL), and then is dried to afford the title compound. Yield: 465 g. Purity by HPLC: 97.81%.

후처리

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 2-3 hours
  3. customwater is removed by azeotropic distillation
  4. additionwater (4000 mL) is added
  5. customOrganic and aqueous layers are separated
  6. washthe organic layer is washed with water (4000 mL)
  7. additionThe pH of combined aqueous layers is adjusted to 1-1.5 by addition of aqueous HCl (100 mL) at 0-5° C
  8. filtrationThe formed solid is collected by filtration
  9. washwashed with water (3000 mL) and hexane (500 mL)
  10. customis dried

출처 및 근거

ORD 기록
ord-eb5f633f4c3d4ccea60b2e25489766ad
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08779161B2

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