Potassium Iodide → HCID 12531863, compound

HRID 1863324Notes

Reaction equation

HRID 1863324 reaction equation
[C:1]1([OH:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.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]>CO.C1C=CC=CC=1.O>[C:1]1([O:11][CH:18]([C:23]2[CH:28]=[CH:27][C:26]([O:29][C:30]3[CH:31]=[CH:32][C:33]([Cl:36])=[CH:34][CH:35]=3)=[CH:25][CH:24]=2)[C:19]([O:21][CH3:22])=[O:20])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 70051-NaphtholHCID 10942334Sodium MethoxideHCID 20392594Methyl alpha-Bromo-alpha-[p-(p-chlorophenoxy)phenyl]acetate

Product 1

HCID 12531863HCID 12531863, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 3.60 g of 1-naphthol, 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 solution is refluxed overnight and then poured into 100 ml of water. The mixture is extracted with 2×75 ml of ether. The combined extracts are washed with 2×50 ml of 5% NaOH, 50 ml of water, saturated brine and dried (MgSO4). Evaporation of the solvent yields a red oil. Chromatography on 100 g of silica gel (benzene, 400 ml) affords a pink oil which solidifies on trituration with petroleum ether to yield a pink solid, mp 107°-109.5° C.

Workup

  1. temperatureThe solution is refluxed overnight
  2. extractionThe mixture is extracted with 2×75 ml of ether
  3. washThe combined extracts are washed with 2×50 ml of 5% NaOH, 50 ml of water, saturated brine
  4. dry with materialdried (MgSO4)
  5. customEvaporation of the solvent
  6. customyields a red oil
  7. customChromatography on 100 g of silica gel (benzene, 400 ml) affords a pink oil which
  8. customto yield a pink solid, mp 107°-109.5° C.

Sources & evidence

ORD record
ord-f525b103a1174aaa9cd500b1ef1b72c0
Source dataset
uspto-grants-1979_09
Patent number
US04168385

Reaction notes

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