Acetylresorcinol → Acetic acid 3-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-phenyl ester

HRID 1994074Notes

Reaction equation

HRID 1994074 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([O:8][C:9](=[O:11])[CH3:10])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:19][C:20]1[N:21]=[C:22]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[O:23][C:24]=1[CH3:25]>CN(C=O)C.C(OCC)(=O)C>[CH3:25][C:24]1[O:23][C:22]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[N:21][C:20]=1[CH2:19][O:1][C:2]1[CH:3]=[C:4]([O:8][C:9](=[O:11])[CH3:10])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 5055AcetylresorcinolHCID 11430Potassium CarbonateHCID 97942894-(Chloromethyl)-5-methyl-2-phenyl-1,3-oxazole

Product 1

HCID 68677549Acetic acid 3-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-phenyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of acetic acid 3-hydroxyphenyl ester (5.0 g, 32.86 mmol) and potassium carbonate (6.8 g, 49.3 mmol) in DMF (40 mL) is added 4-chloromethyl-5-methyl-2-phenyl-oxazole (6.8 g, 32.86 mmol) at RT. The reaction mixture is stirred for 3 h at RT followed by 24 h at 70° C. The reaction mixture is cooled to RT, diluted with ethyl acetate, washed with water and brine, dried over anhydrous magnesium sulfate and concentrated at reduced pressure. The crude product is purified on a Biotage 40M column using 20% ethyl acetate in hexane to yield acetic acid-3-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-phenyl ester as a clear oil.

Workup

  1. waitfollowed by 24 h at 70° C
  2. temperatureThe reaction mixture is cooled to RT
  3. washwashed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated at reduced pressure
  6. customThe crude product is purified on a Biotage 40M column

Sources & evidence

ORD record
ord-8b357ff356314f2ba3351270e5e4c3ad
Source dataset
uspto-grants-2010_01
Patent number
US07652061B2

Reaction notes

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