Toluene → tert-Octylamine

HRID 1200283Notes

Reaction equation

HRID 1200283 reaction equation
[C:1]([C:5]1[C:6]([OH:21])=[C:7]([C:12]([CH3:20])([CH3:19])[CH2:13][CH2:14][CH2:15][C:16](O)=[O:17])[CH:8]=[C:9]([CH3:11])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].S(Cl)(Cl)=O.C1(C)C=CC=CC=1.[CH3:33][C:34]([NH2:41])([CH3:40])[CH2:35][C:36]([CH3:39])([CH3:38])[CH3:37]>CCOCC>[C:1]([C:5]1[C:6]([OH:21])=[C:7]([C:12]([CH3:20])([CH3:19])[CH2:13][CH2:14][CH2:15][C:16]([NH2:41])=[O:17])[CH:8]=[C:9]([CH3:11])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:33][C:34]([NH2:41])([CH3:40])[CH2:35][C:36]([CH3:39])([CH3:38])[CH3:37]

Participants

7

Reactant 4

HCID 1140Toluene2×HCID 24386Thionyl ChlorideHCID 61017tert-OctylamineHCID 19864927HCID 19864927, compound

Product 2

HCID 61017tert-OctylamineHCID 54130444HCID 54130444, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2.0 Parts of 5-(3-t-butyl-2-hydroxy-5-methyl-phenyl)-5-methylhexanoic acid and 2.0 parts thionyl chloride in 25 parts of toluene were stored for 2 hours at room temperature. The toluene and other volatiles were then stripped off at room temperature and 16 mb pressure. To the residue was then added 10 parts of 1,1,3,3-tetramethyl-butylamine and this mixture heated for 3 hours on a steam-bath. After diluting the reaction mixture with ether, the ether solution was washed successively with dilute hydrochloric acid, water, dilute sodium hydroxide, and water. Evaporation of the ether and crystallisation from 60°-80° C. petroleum-ether gave 5-(3-t-butyl-2-hydroxy-5-methylphenyl)-5-methyl-hexanoic acid amide of 1,1,3,3-tetramethylbutylamine m.p. 110°-2° C. with the following percentage composition by weight.

Workup

  1. customwere then stripped off at room temperature
  2. temperaturethis mixture heated for 3 hours on a steam-bath
  3. washthe ether solution was washed successively with dilute hydrochloric acid, water, dilute sodium hydroxide, and water
  4. customEvaporation of the ether and crystallisation from 60°-80° C. petroleum-ether

Sources & evidence

ORD record
ord-cc93b72acb2c4c639fa11312850fe444
Source dataset
uspto-grants-1990_02
Patent number
US04904815

Reaction notes

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