4-Chlorophenol → 2-(2-(4-Chlorophenoxy)phenyl)acetic acid
Reaction equation
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]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 27.5 °C
Procedure
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%.
Workup
- temperatureThe mixture is heated
- temperatureat reflux for 2-3 hours
- customwater is removed by azeotropic distillation
- additionwater (4000 mL) is added
- customOrganic and aqueous layers are separated
- washthe organic layer is washed with water (4000 mL)
- additionThe pH of combined aqueous layers is adjusted to 1-1.5 by addition of aqueous HCl (100 mL) at 0-5° C
- filtrationThe formed solid is collected by filtration
- washwashed with water (3000 mL) and hexane (500 mL)
- customis dried
Sources & evidence
- ORD record
- ord-eb5f633f4c3d4ccea60b2e25489766ad
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08779161B2
Reaction notes
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