p-Toluenesulfonic acid → t-Butylphenol 2-Phenyl-2-oxazoline

HRID 1379178Notes

Reaction equation

HRID 1379178 reaction equation
[C:1]1([C:7]2[O:8][CH2:9][CH2:10][N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:12]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[OH:22])([CH3:15])([CH3:14])[CH3:13].CC1C=CC(S(O)(=O)=O)=CC=1>O1CCCC1>[C:12]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[OH:22])([CH3:15])([CH3:13])[CH3:14].[C:1]1([C:7]2[O:8][CH2:9][CH2:10][N:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 69232-Tert-ButylphenolHCID 2440302-Phenyl-2-oxazoline

Product 1

HCID 86750688t-Butylphenol 2-Phenyl-2-oxazoline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
170 °C

Procedure

A pure sample of the addition product of t-butylphenol and 2-phenyl-2-oxazoline was obtained for comparative purposes as follows: in a side-armed test tube, 2.94 grams 2-phenyl-2-oxazoline and 3.00 grams t-butyl phenol were combined with 0.08 gram pTSA. The stirred mixture was heated under nitrogen at 170° C. for 16 hours. Pure amide ether addition product [B] was obtained from the reaction mixture by column chromatography on silica gel. The crude reaction mixture was taken up in tetrahydrofuran and introduced onto the column, which was subsequently eluted with 1/1 (v/v) hexane/ethyl acetate. Desired fractions were identified by thin layer chromatography, and the product structure was confirmed by 1H and 13C NMR. The reaction is outlined in Scheme 1. ##STR3##

Workup

  1. customwas obtained from the reaction mixture by column chromatography on silica gel
  2. customThe crude reaction mixture
  3. additionintroduced onto the column, which
  4. washwas subsequently eluted with 1/1 (v/v) hexane/ethyl acetate

Sources & evidence

ORD record
ord-72ac9f3f79b54ace94200e96d5e8bc2e
Source dataset
uspto-grants-1997_09
Patent number
US05670590

Reaction notes

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