Stearyl Alcohol → HCID 54410881, compound

HRID 851520Notes

Reaction equation

HRID 851520 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[C:5]([OH:12])=[CH:4][C:3]=1[CH2:13][C:14]([OH:16])=[O:15].[CH2:17](O)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]>C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:9])[CH3:10])[C:5]([OH:12])=[CH:4][C:3]=1[CH2:13][C:14]([O:16][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH3:17])=[O:15]

Participants

5

Reactant 2

HCID 8221Stearyl AlcoholHCID 20501407HCID 20501407, compound

Product 1

HCID 54410881HCID 54410881, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

Into a 300-ml four-necked flask, were charged 22.2 g of 2-methyl-4-t-butyl-5-hydroxyphenylacetic acid, 150 ml of toluene, 27.0 g of octadecyl alcohol and 1 g of p-toluenesulfonic acid. The mixture was heated under reflux for about one hour while removing the liberated water from the reaction system. After completion of the reaction, the reaction mixture was freed from the catalyst by washing with water and from the solvent by distillation under reduced pressure to obtain 45.0 g (95% yield) of pale yellow octadecyl 2-methyl-4-t-butyl-5-hydroxyphenylacetate which was recrystallized from methanol to yield white crystals melting at 53.0°-54.5° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for about one hour
  3. customwhile removing the liberated water from the reaction system
  4. customAfter completion of the reaction
  5. washby washing with water and from the solvent by distillation under reduced pressure

Sources & evidence

ORD record
ord-ef443c23cfde483ca0856928050d2c8f
Source dataset
uspto-grants-1983_05
Patent number
US04385143

Reaction notes

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