Stearyl Alcohol → HCID 14274826, compound

HRID 1681225Notes

Reaction equation

HRID 1681225 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])[CH:8]=[C:9]([CH3:12])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].[CH2:19](O)[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][CH2:34][CH2:35]C>C1(C)C=CC=CC=1.C([Sn](=O)CCCC)CCC>[C:1]([C:5]1[CH:6]=[C:7]([CH2:13][CH2:14][C:15]([O:17][CH2:18][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][CH2:22][CH2:21][CH2:20][CH3:19])=[O:16])[CH:8]=[C:9]([CH3:12])[C:10]=1[OH:11])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 8221Stearyl AlcoholHCID 165455Benzenepropanoic acid, 3-(1,1-dimethylethyl)-4-hydroxy-5-methyl-, methyl ester

Product 1

HCID 14274826HCID 14274826, compoundYield 99.5%

Reagents, catalysts & solvents 2

HCID 61221Dibutyltin oxideCatalystHCID 1140TolueneSolvent

Procedure

Methyl 3-(3-tert-butyl-5-methyl-4-hydroxyphenyl)propionate (70.0 g), octadecyl alcohol (76.3 g) and dibutyltin oxide (0.74 g) were dissolved in toluene (70 ml), after which the mixture was heated, and the solvent (200 ml) was distilled off while adding toluene. The toluene was distilled off from the reaction mixture and the residue was purified by column chromatography to give octadecyl 3-(3-tert-butyl-5-methyl-4-hydroxyphenyl)propionate (136.0 g), m.p. 58°-59° C.

Workup

  1. temperatureafter which the mixture was heated
  2. distillationthe solvent (200 ml) was distilled off
  3. additionwhile adding toluene
  4. distillationThe toluene was distilled off from the reaction mixture
  5. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-2556cbdcd7be449596cb590c45d8cc30
Source dataset
uspto-grants-1992_12
Patent number
US05169885

Reaction notes

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