2-Amino-4-tert-butylphenol → 5-(tert-Butyl)-2-methylbenzoxazole

HRID 339298Notes

Reaction equation

HRID 339298 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[OH:12].Cl.[C:14](=N)(OC)[CH3:15]>CO>[C:8]([C:6]1[CH:5]=[CH:4][C:3]2[O:12][C:14]([CH3:15])=[N:1][C:2]=2[CH:7]=1)([CH3:9])([CH3:11])[CH3:10]

Participants

4

Reactant 2

HCID 709822-Amino-4-tert-butylphenolHCID 10313100Ethanimidic acid, methyl ester, hydrochloride (1:1)

Product 1

HCID 125954135-(tert-Butyl)-2-methylbenzoxazoleYield 24%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a 100 ml round bottom flask was placed 7.25 g (0.044 mol) of 2-Amino-4-tert-butylphenol, (Aldrich Cat #193282) with 6.0 g (0.055 mol) of Methyl acetimidate hydrochloride (Aldrich Cat #254940) with 50 ml of MeOH. This was refluxed for 4 hours. Then the MeOH was removed under vacuum. This was separated between 50 ml of ether and 50 ml of water. The ether was separated, dried, and removed under vacuum. Then 50 ml of hexanes was added to the resulting solid. Remaining 2-Amino-4-tert-butylphenol was insoluble in hexanes and was removed by filtration. The remaining oil was chromatographed using 2% MeOH/CH2Cl2 to provide 5-tert-butyl-2-methylbenzoxazole (Yield=2 g, 24%).

Workup

  1. customIn a 100 ml round bottom flask was placed
  2. temperatureThis was refluxed for 4 hours
  3. customThen the MeOH was removed under vacuum
  4. customThis was separated between 50 ml of ether and 50 ml of water
  5. customThe ether was separated
  6. customdried
  7. customremoved under vacuum
  8. additionThen 50 ml of hexanes was added to the resulting solid
  9. customwas removed by filtration
  10. customThe remaining oil was chromatographed

Sources & evidence

ORD record
ord-4f8e68d288d241cc9dd11a788066fc17
Source dataset
uspto-grants-2014_11
Patent number
US08894976B2

Reaction notes

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