Potassium Iodide → Methyl alpha-(2-naphthyloxy)-alpha-[p-(p-chlorophenoxy)phenyl]acetate

HRID 1704064Notes

Reaction equation

HRID 1704064 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[OH:11].C[O-].[Na+].[I-].[K+].Br[CH:18]([C:23]1[CH:28]=[CH:27][C:26]([O:29][C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=2)=[CH:25][CH:24]=1)[C:19]([O:21][CH3:22])=[O:20]>C1C=CC=CC=1.O>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[O:11][CH:18]([C:23]1[CH:28]=[CH:27][C:26]([O:29][C:30]2[CH:31]=[CH:32][C:33]([Cl:36])=[CH:34][CH:35]=2)=[CH:25][CH:24]=1)[C:19]([O:21][CH3:22])=[O:20]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 86632-NaphtholHCID 10942334Sodium MethoxideHCID 20392594Methyl alpha-Bromo-alpha-[p-(p-chlorophenoxy)phenyl]acetate

Product 1

HCID 12531867Methyl alpha-(2-naphthyloxy)-alpha-[p-(p-chlorophenoxy)phenyl]acetate

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

To a solution of 3.60 g of 2-naphthol, 1.19 g of sodium methoxide and 50 mg of potassium iodide is added 7.11 g of methyl α-bromo-α-[p-(p-chlorophenoxy)phenyl]acetate in 10 ml of benzene. The solution is maintained at reflux overnight and then poured into 100 ml of water. The mixture is then extracted with 2 × 75 ml of ether and the combined extracts are washed with 2 × 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 green glass. Further elution with 200 ml of benzene yields the product as a glass.

Workup

  1. temperatureThe solution is maintained
  2. temperatureat reflux overnight
  3. extractionThe mixture is then extracted with 2 × 75 ml of ether
  4. washthe combined extracts are washed with 2 × 50 ml of 5% NaOH, 50 ml of water, 50 ml of saturated brine
  5. dry with materialdried (MgSO4)
  6. customEvaporation of the solvent
  7. customyields a yellow oil
  8. customChromatography on 100 g of silica gel (benzene, 400 ml) yields a green glass
  9. washFurther elution with 200 ml of benzene

Sources & evidence

ORD record
ord-62715894ebba4591a19b04926754f003
Source dataset
uspto-grants-1978_11
Patent number
US04125729

Reaction notes

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