Potassium Iodide → HCID 12531865, compound

HRID 1863323Notes

Reaction equation

HRID 1863323 reaction equation
[C:1]1([OH:11])[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=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>[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[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 682585,6,7,8-Tetrahydro-1-naphtholHCID 10942334Sodium MethoxideHCID 20392594Methyl alpha-Bromo-alpha-[p-(p-chlorophenoxy)phenyl]acetate

Product 1

HCID 12531865HCID 12531865, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 887MethanolSolvent

Procedure

To a solution of 3.70 g of 5,6,7,8-tetrahydro-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 mixture is refluxed overnight. After cooling to room temperature, the mixture is extracted with 2×75 ml of ether. 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 the product as a yellow 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

Sources & evidence

ORD record
ord-64817e19473a4fea92052e10c8db7fb7
Source dataset
uspto-grants-1979_09
Patent number
US04168385

Reaction notes

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