Potassium Iodide → Methyl alpha-[p-(Benzyloxy)phenoxy]-alpha-[p-(p-chlorophenoxy)phenyl]acetate

HRID 1863304Notes

Reaction equation

HRID 1863304 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O-].[Na+].[I-].[K+].Br[CH:22]([C:27]1[CH:32]=[CH:31][C:30]([O:33][C:34]2[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=2)=[CH:29][CH:28]=1)[C:23]([O:25][CH3:26])=[O:24]>CO.C1C=CC=CC=1.CC(C)=O.CCCCCC.O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][CH:22]([C:27]2[CH:32]=[CH:31][C:30]([O:33][C:34]3[CH:35]=[CH:36][C:37]([Cl:40])=[CH:38][CH:39]=3)=[CH:29][CH:28]=2)[C:23]([O:25][CH3:26])=[O:24])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

10

Reactant 4

HCID 4875Potassium IodideHCID 7638MonobenzoneHCID 10942334Sodium MethoxideHCID 20392594Methyl alpha-Bromo-alpha-[p-(p-chlorophenoxy)phenyl]acetate

Product 1

HCID 12531853Methyl alpha-[p-(Benzyloxy)phenoxy]-alpha-[p-(p-chlorophenoxy)phenyl]acetate

Reagents, catalysts & solvents 5

HCID 180AcetoneSolventHCID 241BenzeneSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 8058HexaneSolvent

Procedure

To a solution of 5.0 g of p-benzyloxyphenol and 1.19 g of sodium methoxide in 40 ml of methanol is added 50 mg of potassium iodide and 7.11 g of methyl α-bromo-α-[p-(p-chlorophenoxy)phenyl]acetate in 10 ml of benzene. The mixture is refluxed for 22 hours and poured into ice and water. The mixture is extracted with ether and the ether extracts washed with 10% potassium carbonate and with water. The extracts are dried (MgSO4) and the solvent removed under vacuum to give an oily solid. Trituration with hexane plus a small amount of acetone and chilling gives crystals. Filtration gives the product as off-white crystals, mp 91°-96° C. Recrystallization by dissolving in hot acetone, diluting with petroleum ether, chilling and filtering gives the product as white crystals, mp 88°-90° C.

Workup

  1. temperatureThe mixture is refluxed for 22 hours
  2. extractionThe mixture is extracted with ether
  3. washthe ether extracts washed with 10% potassium carbonate and with water
  4. dry with materialThe extracts are dried (MgSO4)
  5. customthe solvent removed under vacuum
  6. customto give an oily solid
  7. customgives crystals
  8. filtrationFiltration

Sources & evidence

ORD record
ord-e82a42ac1818417cb60d316b7900913f
Source dataset
uspto-grants-1979_09
Patent number
US04168385

Reaction notes

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