2-Ethylhexanol → HCID 54546381, compound

HRID 1461888Notes

Reaction equation

HRID 1461888 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])[CH:8]=[CH:9][C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].[CH2:18]([CH:20]([CH2:23][CH2:24][CH2:25][CH3:26])CO)[CH3:19]>C([Sn](=O)CCCC)CCC.C1(C)C=CC=CC=1>[C:1]([C:5]1[CH:6]=[C:7]([CH2:12][CH2:13][C:14]([O:16][CH2:17][CH:20]([CH2:18][CH3:19])[CH2:23][CH2:24][CH2:25][CH3:26])=[O:15])[CH:8]=[CH:9][C:10]=1[OH:11])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 77202-EthylhexanolHCID 3084638Benzenepropanoic acid, 3-(1,1-dimethylethyl)-4-hydroxy-, methyl ester

Product 1

HCID 54546381HCID 54546381, compoundYield 94.6%

Reagents, catalysts & solvents 2

HCID 61221Dibutyltin oxideCatalystHCID 1140TolueneSolvent2×

Conditions

Temperature
140 °C

Procedure

A mixture of 45 g of methyl 3-(3-tert-butyl-4-hydroxyphenyl)propionate, 24.7 g of 2-ethylhexylalcohol, 0.5 g of dibutyltin oxide and 50 ml of toluene was heated to 140° C., whereto toluene was further added while the solvent was being distilled off. After the mixture was stirred for 10 hours, toluene was distilled off. The obtained residue was purified by silica gel column chromatography to give 60 g of 2-ethylhexyl 3-(3-tert-butyl-4-hydroxyphenyl)propionate as a pale yellow oily substance.

Workup

  1. distillationwas being distilled off
  2. distillationtoluene was distilled off
  3. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e0873a5df8554f218e40c9abdce6c4c7
Source dataset
uspto-grants-1991_12
Patent number
US05077424

Reaction notes

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