Stearyl Alcohol → Octadecyl DI-tert-butyl-4-hydroxyhydrocinnamate

HRID 1815684Notes

Reaction equation

HRID 1815684 reaction equation
[CH3:1][O:2][C:3](=[O:21])[CH2:4][CH2:5][C:6]1[CH:11]=[C:10]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:9]([OH:16])=[C:8]([C:17]([CH3:20])([CH3:19])[CH3:18])[CH:7]=1.[CH2:22](O)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]C.C([O-])(=O)C.[Li+]>CO>[CH2:1]([O:2][C:3](=[O:21])[CH2:4][CH2:5][C:6]1[CH:7]=[C:8]([C:17]([CH3:20])([CH3:19])[CH3:18])[C:9]([OH:16])=[C:10]([C:12]([CH3:14])([CH3:13])[CH3:15])[CH:11]=1)[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH3:22]

Participants

5

Reactant 3

HCID 8221Stearyl AlcoholHCID 62603Methyl di-t-butyl hydroxyhydrocinnamateHCID 3474584Lithium acetate

Product 1

HCID 16386Octadecyl DI-tert-butyl-4-hydroxyhydrocinnamateYield 96.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

109 g (0.374 mol) of β-(3,5-di-tert-butyl4-hydroxyphenyl)propionic acid methyl ester, 92.5 g (0.34 mol) of stearyl alcohol and 0.1 g of lithium acetate in the dihydrate form (0.001 mol) are introduced into a vessel and melted and stirred at 100° C. under nitrogen. As soon as a melt is obtained, cautiously evacuation is carried out and at the same time the melt is heated to an internal temperature (IT) of from 150 to 160° C. The methanol formed is distilled off and condensed in a cold trap. As soon as an internal pressure of <10 mbar is reached, the internal temperature (IT) is increased to from 170 to 180° C. and further evacuation to <1 mbar is carried out. As soon as IT=180° C. and a pressure of <1 mbar is reached, those conditions are maintained for one hour and then, in the course of from 1 to 2 hours at IT=200-210° C., the excess β-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid methyl ester is removed by distillation. The reaction melt then contains <0.2% starting materials and has a content of >98% β-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid octadecyl ester. The reaction melt is cooled, and left to stand for crystallisation. Yield 96.5%; m.p. 51° C.

Workup

  1. customAs soon as a melt is obtained
  2. temperatureis heated to an internal temperature (IT) of from 150 to 160° C
  3. distillationis distilled off
  4. customcondensed in a cold trap
  5. temperaturethe internal temperature (IT) is increased to from 170 to 180° C. and further evacuation to <1 mbar
  6. customsoon as IT=180° C.
  7. temperaturethose conditions are maintained for one hour
  8. customin the course of from 1 to 2 hours at IT=200-210° C., the excess β-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid methyl ester is removed by distillation
  9. temperatureThe reaction melt is cooled
  10. waitleft
  11. customto stand for crystallisation

Sources & evidence

ORD record
ord-7e00740feef142e7b22dc56a5234df5c
Source dataset
uspto-grants-2005_04
Patent number
US06878843B2

Reaction notes

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