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

HRID 1625162ノート

反応式

HRID 1625162 の反応式
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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23978Copper触媒HCID 7237O-Xylene溶媒

反応条件

温度
27.5 °C

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-eb5f633f4c3d4ccea60b2e25489766ad
出典データセット
uspto-grants-2014_07
特許番号
US08779161B2

反応ノート

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