4-Chloro-3-methylphenol → Methyl (4-chloro-3-methylphenoxy)[p-(p-chlorophenoxy)phenyl]acetate

HRID 1863322Notes

Reaction equation

HRID 1863322 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH3:9].C[O-].[Na+].[I-].[K+].Br[CH:16]([C:21]1[CH:26]=[CH:25][C:24]([O:27][C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=2)=[CH:23][CH:22]=1)[C:17]([O:19][CH3:20])=[O:18]>CO.C1C=CC=CC=1.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:16]([C:21]2[CH:26]=[CH:25][C:24]([O:27][C:28]3[CH:29]=[CH:30][C:31]([Cl:34])=[CH:32][CH:33]=3)=[CH:23][CH:22]=2)[C:17]([O:19][CH3:20])=[O:18])=[CH:4][C:3]=1[CH3:9]

Participants

8

Reactant 4

HCID 17324-Chloro-3-methylphenolHCID 4875Potassium IodideHCID 10942334Sodium MethoxideHCID 20392594Methyl alpha-Bromo-alpha-[p-(p-chlorophenoxy)phenyl]acetate

Product 1

HCID 12531906Methyl (4-chloro-3-methylphenoxy)[p-(p-chlorophenoxy)phenyl]acetate

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 3.565 g of 4-chloro-3-methylphenol, 1.188 g of sodium methoxide and 50 mg of potassium iodide in 40 ml of methanol is added 7.11 g of methyl α-bromo-α-[p-(p-chlorophenoxy)phenyl]acetate in 10 ml of benzene. The mixture is refluxed overnight and poured into 100 ml of water. The mixture is extracted with 2×75 ml of ether and the combined extracts are washed with 50 ml of 5% NaOH, 50 ml of water, 50 ml of saturated brine and dried (MgSO4). Evaporation of the solvent yields a yellow oil. Chromatography on 100 g of silica gel yields a colorless oil.

Workup

  1. temperatureThe mixture is refluxed overnight
  2. extractionThe mixture is extracted with 2×75 ml of ether
  3. washthe combined extracts are washed with 50 ml of 5% NaOH, 50 ml of water, 50 ml of saturated brine
  4. dry with materialdried (MgSO4)
  5. customEvaporation of the solvent
  6. customyields a yellow oil
  7. customChromatography on 100 g of silica gel yields a colorless oil

Sources & evidence

ORD record
ord-7985208701084316a532e3ad212ab10e
Source dataset
uspto-grants-1979_09
Patent number
US04168385

Reaction notes

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