Potassium Iodide → Methyl (5-indanyloxy)[p-(p-chlorophenoxy)phenyl]acetate

HRID 1704063Notes

Reaction equation

HRID 1704063 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([OH:10])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.C[O-].[Na+].[I-].[K+].Br[CH:17]([C:22]1[CH:27]=[CH:26][C:25]([O:28][C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=2)=[CH:24][CH:23]=1)[C:18]([O:20][CH3:21])=[O:19]>CO.C1C=CC=CC=1.O>[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([O:10][CH:17]([C:22]3[CH:27]=[CH:26][C:25]([O:28][C:29]4[CH:30]=[CH:31][C:32]([Cl:35])=[CH:33][CH:34]=4)=[CH:24][CH:23]=3)[C:18]([O:20][CH3:21])=[O:19])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 151185-IndanolHCID 10942334Sodium MethoxideHCID 20392594Methyl alpha-Bromo-alpha-[p-(p-chlorophenoxy)phenyl]acetate

Product 1

HCID 12531866Methyl (5-indanyloxy)[p-(p-chlorophenoxy)phenyl]acetate

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 3.36 g of 5-indanol, 1.19 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 added to 100 ml of water. The mixture is then 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 (benzene, 400 ml) yields a light yellow oil.

Workup

  1. temperatureThe mixture is refluxed overnight
  2. extractionThe mixture is then 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 (benzene, 400 ml) yields a light yellow oil

Sources & evidence

ORD record
ord-db082abda00d40c58822fc31e1c89ccd
Source dataset
uspto-grants-1978_11
Patent number
US04125729

Reaction notes

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