Potassium Iodide → Methyl alpha-(4-chloro-5,6,7,8-tetrahydro-1-naphthyloxy)-alpha-[p-(p-chlorophenoxy)phenyl]acetate

HRID 1863333

Reaction equation

HRID 1863333 reaction equation
C[O-].[Na+].[Cl:4][C:5]1[C:14]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=2[C:8]([OH:15])=[CH:7][CH:6]=1.[I-].[K+].Br[CH:19]([C:24]1[CH:29]=[CH:28][C:27]([O:30][C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=2)=[CH:26][CH:25]=1)[C:20]([O:22][CH3:23])=[O:21]>C1C=CC=CC=1.O>[Cl:4][C:5]1[C:14]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=2[C:8]([O:15][CH:19]([C:24]2[CH:29]=[CH:28][C:27]([O:30][C:31]3[CH:32]=[CH:33][C:34]([Cl:37])=[CH:35][CH:36]=3)=[CH:26][CH:25]=2)[C:20]([O:22][CH3:23])=[O:21])=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10942334Sodium MethoxideHCID 202033334-Chloro-5,6,7,8-tetrahydronaphthalen-1-olHCID 20392594Methyl alpha-Bromo-alpha-[p-(p-chlorophenoxy)phenyl]acetate

Product 1

HCID 12531871Methyl alpha-(4-chloro-5,6,7,8-tetrahydro-1-naphthyloxy)-alpha-[p-(p-chlorophenoxy)phenyl]acetate

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

To a solution of 1.19 g of sodium methoxide, 4.57 g of 4-chloro-5,6,7,8-tetrahydro-1-naphthol, and 100 mg of potassium iodide was added 7.11 g of methyl α-bromo-α-[p-(p-chlorophenoxy)phenyl]acetate in 10 ml of benzene. The mixture was heated at reflux overnight, cooled to room temperature, and poured into 100 ml of water. The mixture was then extracted with 2×75 ml of ether. The combined extracts were washed with 2×50 ml of 5% NaOH, 2×50 ml of water, 50 ml of saturated brine, and dried (MgSO4). Evaporation of the solvent yielded an oil which was chromatographed over 100 g of silica gel (benzene). Concentration of cuts yielded a yellow gum which solidified on standing to give the product as a white solid, mp 87.5°-90° C. (6.4 g).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. extractionThe mixture was then extracted with 2×75 ml of ether
  4. washThe combined extracts were washed with 2×50 ml of 5% NaOH, 2×50 ml of water, 50 ml of saturated brine
  5. dry with materialdried (MgSO4)
  6. customEvaporation of the solvent
  7. customyielded an oil which
  8. customwas chromatographed over 100 g of silica gel (benzene)
  9. customConcentration of cuts yielded a yellow gum which

Sources & evidence

ORD record
ord-740e6d6ca3204dcc9b4ca04665a9ca90
Source dataset
uspto-grants-1979_09
Patent number
US04168385

Linked notes

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