Acetaminophen → Methyl 4-(4-acetamidophenoxy)benzoate

HRID 23374

Reaction equation

HRID 23374 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].[CH3:12][O:13][C:14]([C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1)=[O:15]>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][C:19]2[CH:20]=[CH:21][C:16]([C:14]([O:13][CH3:12])=[O:15])=[CH:17][CH:18]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 1983AcetaminophenHCID 27343694-Methoxycarbonylphenylboronic acid

Product 1

HCID 22573305Methyl 4-(4-acetamidophenoxy)benzoateYield 75.1%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

Dry air is bubbled through a solution of 4-acetamidophenol (320 mg, 2.1 mmol), copper(II) acetate (384 mg, 2.1 mmol), TEA (1.5 mL, 10.5 mol), (4-methoxycarbonylphenyl)boronic acid (760 mg, 4.2 mmol), and powdered molecular sieves (2 g) in CH2Cl2 (21 mL) for 16 hours at room temperature. The resulting material is concentrated and purified by flash column chromatography (25-50% EtOAc in heptane) to give methyl 4-(4-acetamidophenoxy)benzoate (450 mg, 75%). 1H NMR (300 MHz, DMSO) δ 8.01, 7.54, 7.27, 7.05, 6.98, 3.92, 2.22.

Workup

  1. customDry air
  2. customfor 16 hours
  3. customat room temperature
  4. concentrationThe resulting material is concentrated
  5. custompurified by flash column chromatography (25-50% EtOAc in heptane)

Sources & evidence

ORD record
ord-6135df3391b94ab680a5652fa0de43f5
Source dataset
uspto-grants-2005_02
Patent number
US06852716B2

Linked notes

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