p-Toluenesulfonic acid monohydrate → 2-(3-Methoxy-4-methylphenyl)-1,3-benzoxazole

HRID 7731

Reaction equation

HRID 7731 reaction equation
O[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:19])[C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[C:12]([O:17][CH3:18])[CH:11]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:18][O:17][C:12]1[CH:11]=[C:10]([C:9]2[O:19][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[N:8]=2)[CH:15]=[CH:14][C:13]=1[CH3:16]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 16378794N-(2-Hydroxyphenyl)-3-methoxy-4-methylbenzamide

Product 1

HCID 219909682-(3-Methoxy-4-methylphenyl)-1,3-benzoxazole

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of N-(2-hydroxyphenyl)-3-methoxy-4-methylbenzamide (1.5 g, 5.8 mmol), toluene (30 mL), p-toluenesulfonic acid monohydrate (7.6 g, 40 mmol) and molecular sieves was refluxed overnight. After cooling reaction to rt, filtered washing with warm chloroform and concentrated filtrate in vacuo. The resulting brown oil was purified by flash chromatography on silica gel using 1:4 EtOAc:hexanes to give the desired intermediate, 2-(3-methoxy-4-methylphenyl)-1,3-benzoxazole, as a colorless solid.

Workup

  1. temperaturewas refluxed overnight
  2. temperatureAfter cooling
  3. customreaction to rt
  4. filtrationfiltered
  5. washwashing with warm chloroform and concentrated filtrate in vacuo
  6. customThe resulting brown oil was purified by flash chromatography on silica gel using 1:4 EtOAc

Sources & evidence

ORD record
ord-04560bce4f774e089189eeafb357a37c
Source dataset
uspto-grants-2006_08
Patent number
US07087601B2

Linked notes

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