Water → HCID 12531885, compound

HRID 1863335Notes

Reaction equation

HRID 1863335 reaction equation
C[O-].[Na+].[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.Br[CH:13]([C:18]1[CH:23]=[CH:22][C:21]([O:24][C:25]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:28]([Cl:35])=[CH:27][CH:26]=2)=[CH:20][CH:19]=1)[C:14]([O:16][CH3:17])=[O:15].O>CO.C1C=CC=CC=1.[I-].[K+]>[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH:13]([C:18]2[CH:23]=[CH:22][C:21]([O:24][C:25]3[C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[C:28]([Cl:35])=[CH:27][CH:26]=3)=[CH:20][CH:19]=2)[C:14]([O:16][CH3:17])=[O:15])=[CH:7][CH:6]=1

Participants

8

Reactant 4

HCID 962WaterHCID 46844-ChlorophenolHCID 10942334Sodium MethoxideHCID 20392634HCID 20392634, compound

Product 1

HCID 12531885HCID 12531885, compoundYield 73.8%

Reagents, catalysts & solvents 3

HCID 4875Potassium IodideCatalystHCID 241BenzeneSolventHCID 887MethanolSolvent

Procedure

To a solution of 1.19 g of sodium methoxide, 3.21 g of p-chlorophenol and 50 mg of potassium iodide in 40 ml of methanol was added 8.12 g of methyl α-bromo-α-[p-(4-chloro-1-naphthyloxy)phenyl]acetate in 10 ml of benzene. The mixture was refluxed overnight, cooled to room temperature, and then poured into 100 ml of water. The mixture was 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 saturated brine, and dried (MgSO4). Evaporation of the solvent yielded an amber oil which was subjected to chromatography on 100 g silica gel (benzene) to afford 6.7 g of an amber glass.

Workup

  1. temperatureThe mixture was refluxed overnight
  2. extractionThe mixture was extracted with 2×75 ml of ether
  3. washThe combined extracts were washed with 2×50 ml of 5% NaOH, 2×50 ml of water, 50 ml saturated brine
  4. dry with materialdried (MgSO4)
  5. customEvaporation of the solvent
  6. customyielded an amber oil which

Sources & evidence

ORD record
ord-04cf57ac83ef46e2936f609c99488d22
Source dataset
uspto-grants-1979_09
Patent number
US04168385

Reaction notes

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