Stearic Acid → 3-Stearamidopropyl 3(3,5-di-tert-butyl-4-hydroxyphenyl)propionate

HRID 1659905Notes

Reaction equation

HRID 1659905 reaction equation
C(O)(=O)CCCCCCCCCCCCCCCCC.NCCCO.C[O-].[Na+].[OH:29][CH2:30][CH2:31][CH2:32][NH:33][C:34](=[O:52])[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51].[C:53]([C:57]1[CH:58]=[C:59]([CH2:68][CH2:69][C:70](O)=[O:71])[CH:60]=[C:61]([C:64]([CH3:67])([CH3:66])[CH3:65])[C:62]=1[OH:63])([CH3:56])([CH3:55])[CH3:54]>CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-].[Ti+4].C1(C)C(C)=CC=CC=1.CCCCCC.O>[C:64]([C:61]1[CH:60]=[C:59]([CH2:68][CH2:69][C:70]([O:29][CH2:30][CH2:31][CH2:32][NH:33][C:34](=[O:52])[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51])=[O:71])[CH:58]=[C:57]([C:53]([CH3:55])([CH3:54])[CH3:56])[C:62]=1[OH:63])([CH3:67])([CH3:65])[CH3:66]

Participants

10

Reactant 5

HCID 5281Stearic AcidHCID 90863-Amino-1-propanolHCID 883893-(3',5'-Di-tert-butyl-4'-hydroxyphenyl)propionic acidHCID 3017740N-(3-Hydroxypropyl)octadecanamideHCID 10942334Sodium Methoxide

Product 1

HCID 205584903-Stearamidopropyl 3(3,5-di-tert-butyl-4-hydroxyphenyl)propionate

Reagents, catalysts & solvents 4

HCID 21801Titanium tetrabutoxideCatalystHCID 962WaterSolventHCID 7237O-XyleneSolvent2×HCID 8058HexaneSolvent

Procedure

Stearic acid (56.8 g; 0.2 mole) was added to a hot (80° C.) mixture of 30 g (0.4 mole) 3-aminopropanol, 100 ml xylene and 0.5 g sodium methoxide. The mixture was heated at reflux for two hours with removal of water and was then poured into hexane, in which N-(3-hydroxypropyl)stearamide crystallized and was obtained by filtration; it melted at 83°-89° C. After the product was recrystallized from acetone, melting point rose to 94°-96° C. A 34.1 g (0.1 mole) portion of this intermediate was heated with 27.8 g (0.1 mole) of 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid, 1 g of Tyzor TBT catalyst and 100 ml xylene. After the mixture was refluxed for 3 hours, 2 ml of water was collected in the Stark and Dean trap. The xylene was distilled off under vacuum, and the residue was crystallized from acetonitrile. The title product (29 g) thus obtained melted at 50°-52° C.

Workup

  1. temperatureThe mixture was heated
  2. customcrystallized
  3. customwas obtained by filtration
  4. customAfter the product was recrystallized from acetone
  5. customrose to 94°-96° C
  6. temperatureAfter the mixture was refluxed for 3 hours
  7. custom2 ml of water was collected in the Stark and Dean trap
  8. distillationThe xylene was distilled off under vacuum
  9. customthe residue was crystallized from acetonitrile

Sources & evidence

ORD record
ord-a0058f6ab5c54dc1bbd9da24fd03a616
Source dataset
uspto-grants-1981_12
Patent number
US04305868

Reaction notes

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