Phenol → HCID 20392619, compound

HRID 1704067Notes

Reaction equation

HRID 1704067 reaction equation
[C:1]1(O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:8][O-:9].[Na+].[I-].[K+].Br[CH:14]([C:19]1[CH:24]=[CH:23][C:22]([O:25][C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=2)=[CH:21][CH:20]=1)[C:15]([O:17][CH3:18])=[O:16]>CO.C1C=CC=CC=1>[C:3]12([C:26]3[CH:31]=[CH:30][C:8]([O:9][CH:14]([C:19]4[CH:24]=[CH:23][C:22]([O:25][C:26]5[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=5)=[CH:21][CH:20]=4)[C:15]([O:17][CH3:18])=[O:16])=[CH:28][CH:27]=3)[CH2:4][CH:5]3[CH2:14][CH:19]([CH2:24][CH:1]([CH2:6]3)[CH2:2]1)[CH2:20]2

Participants

7

Reactant 4

HCID 996PhenolHCID 4875Potassium IodideHCID 10942334Sodium MethoxideHCID 20392594Methyl alpha-Bromo-alpha-[p-(p-chlorophenoxy)phenyl]acetate

Product 1

HCID 20392619HCID 20392619, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 887MethanolSolvent

Procedure

To a solution of 5.7 g of p-(1-adamantyl))phenol, 1.19 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. After 20 minutes, a white solid separates. The mixture is refluxed overnight, cooled and filtered to remove the white solid. The solid is heated in 50 ml of hot chloroform and filtered to remove a small amount of insoluble residue. The filtrate is diluted with 50 ml of hexane and filtered to give the product as white crystals, mp 148.4°-150.5° C.

Workup

  1. temperatureThe mixture is refluxed overnight
  2. temperaturecooled
  3. filtrationfiltered
  4. customto remove the white solid
  5. temperatureThe solid is heated in 50 ml of hot chloroform
  6. filtrationfiltered
  7. customto remove a small amount of insoluble residue
  8. additionThe filtrate is diluted with 50 ml of hexane
  9. filtrationfiltered

Sources & evidence

ORD record
ord-632aec735d18488a8bd72282ba7b1962
Source dataset
uspto-grants-1978_11
Patent number
US04125729

Reaction notes

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