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

反応式

[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

参加物

反応条件

温度: 170 °C

実験手順

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##