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

HRID 1704046Notes

Reaction equation

HRID 1704046 reaction equation
C[O-].[Na+].[CH:4]1([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.[I-].[K+].Br[CH:20]([C:25]1[CH:30]=[CH:29][C:28]([O:31][C:32]2[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=2)=[CH:27][CH:26]=1)[C:21]([O:23][CH3:24])=[O:22]>CO.C1C=CC=CC=1.O>[CH:4]1([C:10]2[CH:11]=[CH:12][C:13]([O:16][CH:20]([C:25]3[CH:30]=[CH:29][C:28]([O:31][C:32]4[CH:33]=[CH:34][C:35]([Cl:38])=[CH:36][CH:37]=4)=[CH:27][CH:26]=3)[C:21]([O:23][CH3:24])=[O:22])=[CH:14][CH:15]=2)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]1

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 143274-CyclohexylphenolHCID 10942334Sodium MethoxideHCID 20392594Methyl alpha-Bromo-alpha-[p-(p-chlorophenoxy)phenyl]acetate

Product 1

HCID 20392628Methyl alpha-(p-cyclohexylphenoxy)-alpha-[p-(p-chlorophenoxy)phenyl]acetate

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 1.19 g of sodium methoxide and 4.4 g of p-cyclohexylphenol 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 solution is refluxed overnight, cooled to room temperature and poured into 100 ml of water. The mixture is extracted with two 60 ml portions of ether and the combined extracts washed with two 50 ml portins of 5% sodium hydroxide, 50 ml of water and 50 ml of saturated NaCl. The extract is dried (MgSO4) and the solvent removed under vacuum. The residue is triturated with petroleum ether to give the product as white crystals, mp 122°-123.5° C.

Workup

  1. temperatureThe solution is refluxed overnight
  2. extractionThe mixture is extracted with two 60 ml portions of ether
  3. washthe combined extracts washed with two 50 ml portins of 5% sodium hydroxide, 50 ml of water and 50 ml of saturated NaCl
  4. dry with materialThe extract is dried (MgSO4)
  5. customthe solvent removed under vacuum
  6. customThe residue is triturated with petroleum ether

Sources & evidence

ORD record
ord-63c4c26669294580b7226adc96b4af16
Source dataset
uspto-grants-1978_11
Patent number
US04125729

Reaction notes

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