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Acetaminophen → Methyl alpha-(p-acetamidophenoxy)-alpha-[p-(p-chlorophenoxy)phenyl]acetate

HRID 1704040
Notes
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Reaction equation

HRID 1704040 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].C[O-].[Na+].[I-].[K+].Br[CH:18]([C:23]1[CH:28]=[CH:27][C:26]([O:29][C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=2)=[CH:25][CH:24]=1)[C:19]([O:21][CH3:22])=[O:20]>CO.C1C=CC=CC=1.O>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH:18]([C:23]2[CH:28]=[CH:27][C:26]([O:29][C:30]3[CH:31]=[CH:32][C:33]([Cl:36])=[CH:34][CH:35]=3)=[CH:25][CH:24]=2)[C:19]([O:21][CH3:22])=[O:20])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 1983AcetaminophenHCID 4875Potassium IodideHCID 10942334Sodium MethoxideHCID 20392594Methyl alpha-Bromo-alpha-[p-(p-chlorophenoxy)phenyl]acetate

Product 1

HCID 12531907Methyl alpha-(p-acetamidophenoxy)-alpha-[p-(p-chlorophenoxy)phenyl]acetate

Reagents, catalysts & solvents 3

HCID 241
Benzene
Solvent
HCID 887MethanolSolvent
HCID 962WaterSolvent

Procedure

To a solution of 3.78 g of p-acetamidophenol, 1.1 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 15 ml of benzene. The mixture is refluxed for 20 hours, poured into ice and water and extracted with chloroform. The chloroform extracts are washed with 10% potassium carbonate and with water. The extract is dried over magnesium sulfate and concentrated to a gum under vacuum. Petroleum ether is added to the residue and several ml of acetone. Scratching the flask gives crystals which are filtered to give the product as pink crystals, mp 152°- 157° C. The crystals are dissolved in a minimum amount of hot acetone, the solution chilled and diluted with petroleum ether. Chilling and filtering gives pale pink crystals, mp 157°-160° C.

Workup

  1. temperatureThe mixture is refluxed for 20 hours
  2. extractionextracted with chloroform
  3. washThe chloroform extracts are washed with 10% potassium carbonate and with water
  4. dry with materialThe extract is dried over magnesium sulfate
  5. concentrationconcentrated to a gum under vacuum
  6. additionPetroleum ether is added to the residue and several ml of acetone
  7. customgives crystals which
  8. filtrationare filtered

Sources & evidence

ORD record
ord-477bc9b6df5348bdb5f6dcc97324db4a
Source dataset
uspto-grants-1978_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04125729

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes