Methylparaben → Methyl 4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]benzoate

HRID 644004Notes

Reaction equation

HRID 644004 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[O:6][C:7]=1[CH3:8].[OH:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:23][O:22][C:20](=[O:21])[C:19]1[CH:24]=[CH:25][C:16]([O:15][CH2:2][C:3]2[N:4]=[C:5]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[O:6][C:7]=2[CH3:8])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 7456MethylparabenHCID 11430Potassium CarbonateHCID 97942894-(Chloromethyl)-5-methyl-2-phenyl-1,3-oxazole

Product 1

HCID 11461459Methyl 4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-chloromethyl-5-methyl-2-phenyl-oxazole (3.0 g, 14.4 mmol), methyl 4-hydroxybenzoate (2.64 g, 17.3 mmol), and potassium carbonate (6.0 g, 43.34 mmol) in DMF is stirred at RT overnight. The mixture is then partitioned between EtOAc and water, and the organic phase is washed with brine, dried over magnesium sulfate, and concentrated under vacuum to give the crude product. The material is purified by silica gel chromatography using 15% EtOAc in hexane as the eluent to give 4-(5-methyl-2-phenyl-oxazol-4-ylmethoxy) benzoic acid methyl ester as a white solid.

Workup

  1. customThe mixture is then partitioned between EtOAc and water
  2. washthe organic phase is washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under vacuum
  5. customto give the crude product
  6. customThe material is purified by silica gel chromatography

Sources & evidence

ORD record
ord-a28b4504ad3f48158a4345a7e721899b
Source dataset
uspto-grants-2010_04
Patent number
US07700637B2

Reaction notes

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