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alpha-Tocopherol → alpha-Tocopherol 4-aminobenzoate

HRID 325097
Notes
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Reaction equation

HRID 325097 reaction equation
[CH3:1][C:2]1[C:7]([OH:8])=[C:6]([CH3:9])[C:5]2[CH2:10][CH2:11][C@:12]([CH2:15][CH2:16][CH2:17][C@@H:18]([CH2:20][CH2:21][CH2:22][C@@H:23]([CH2:25][CH2:26][CH2:27][CH:28]([CH3:30])[CH3:29])[CH3:24])[CH3:19])([CH3:14])[O:13][C:4]=2[C:3]=1[CH3:31].[NH2:32][C:33]1[CH:41]=[CH:40][C:36]([C:37](Cl)=[O:38])=[CH:35][CH:34]=1>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[CH3:1][C:2]1[C:7]([OH:8])=[C:6]([CH3:9])[C:5]2[CH2:10][CH2:11][C@:12]([CH2:15][CH2:16][CH2:17][C@@H:18]([CH2:20][CH2:21][CH2:22][C@@H:23]([CH2:25][CH2:26][CH2:27][CH:28]([CH3:30])[CH3:29])[CH3:24])[CH3:19])([CH3:14])[O:13][C:4]=2[C:3]=1[CH3:31].[NH2:32][C:33]1[CH:41]=[CH:40][C:36]([C:37]([O-:8])=[O:38])=[CH:35][CH:34]=1
ParticipantsProcedureSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 14985alpha-TocopherolHCID 177720Benzoyl chloride, 4-amino-

Product 1

HCID 86756642alpha-Tocopherol 4-aminobenzoateYield 68%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

The reaction of alpha-tocopherol with 4-aminobenzoic acid chloride was carried out in the same manner with Example I, except that 10 mol % of 4-(dimethylamino)pyridine was added together with pyridine. This reaction was confirmed to proceed in a similar pattern to that of Example I as measured by thin layer chromatography. The remaining processes of Example I were repeated to produce alpha-tocopherol 4-aminobenzoate (0.61 g, yield 68%).

Sources & evidence

ORD record
ord-84a2330b294a46d5b04e558ac57f83de
Source dataset
uspto-grants-2001_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06222051B1

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes