3,5-Di-tert-butyl-4-hydroxyhydrocinnamic acid hydrazide → N-[3-(3,5-di-t-butyl-4-hydroxyphenyl)propanamido]-2-hexadecylsuccinimide

HRID 2372863Notes

Reaction equation

HRID 2372863 reaction equation
[CH2:1]([CH:17]1[CH2:22][C:21](=[O:23])[O:20][C:18]1=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[C:24]([C:28]1[CH:29]=[C:30]([CH2:39][CH2:40][C:41]([NH:43][NH2:44])=[O:42])[CH:31]=[C:32]([C:35]([CH3:38])([CH3:37])[CH3:36])[C:33]=1[OH:34])([CH3:27])([CH3:26])[CH3:25]>>[C:35]([C:32]1[CH:31]=[C:30]([CH2:39][CH2:40][C:41]([NH:43][N:44]2[C:21](=[O:23])[CH2:22][CH:17]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[C:18]2=[O:20])=[O:42])[CH:29]=[C:28]([C:24]([CH3:25])([CH3:26])[CH3:27])[C:33]=1[OH:34])([CH3:36])([CH3:37])[CH3:38]

Participants

3

Reactant 2

HCID 648653,5-Di-tert-butyl-4-hydroxyhydrocinnamic acid hydrazideHCID 778682,5-Furandione, 3-hexadecyldihydro-

Product 1

HCID 15044324N-[3-(3,5-di-t-butyl-4-hydroxyphenyl)propanamido]-2-hexadecylsuccinimideYield 102.4%

Conditions

Temperature
148 °C

Procedure

2-Hexadecylsuccinic anhydride (10.5 g, 31.3 mmol) was heated to about 115° C. under a nitrogen atmosphere. To this stirred melt was added, in portions, 3-(3,5-di-t-butyl-4hydroxyphenyl)propanoic acid hydrazide (9.2 g, 31.3 mmol). Successive additions of hydrazide required raising the melt temperature to facilitate stirring. The final addition of hydrazide was done at a melt temperature of approximately 135° C. After this final portion was blended into the melt, vacuum was applied and the melt temperature was raised to about 148° C. and maintained at that temperature for 20 minutes. The melt was allowed to cool to approximately 115° C. whereupon the vacuum was released and the clear yellow melt was quickly poured into a container. 19.2 g of a yellow viscous liquid was obtained that solidified to a waxy, translucent white solid upon standing for several days at room temperature. The waxy material was recrystallized from acetone to give a white solid having a melting point of 85° C.

Workup

  1. customwas done at a melt temperature of approximately 135° C
  2. temperaturemaintained at that temperature for 20 minutes
  3. temperatureto cool to approximately 115° C. whereupon the vacuum
  4. additionthe clear yellow melt was quickly poured into a container

Sources & evidence

ORD record
ord-6270b856599d4fc08d1914a0abe92b75
Source dataset
uspto-grants-1992_03
Patent number
US05100940

Reaction notes

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