N,N-Dimethylaniline → 3-(3-Tert-butyl-2-hydroxy-5-methylphenyl)propyl 3-[3-(2-(3,5-di-tert-butyl-4-hydroxyphenyl)ethylcarbonyloxy]propylthio]propionate

HRID 2309282Notes

Reaction equation

HRID 2309282 reaction equation
[C:1]([C:5]1[C:6]([OH:16])=[C:7]([CH2:12][CH2:13][CH2:14][OH:15])[CH:8]=[C:9]([CH3:11])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].CN(C)C1C=CC=CC=1.[C:26]([C:30]1[CH:31]=[C:32]([CH2:41][CH2:42][C:43]([O:45][CH2:46][CH2:47][CH2:48][S:49][CH2:50][CH2:51][C:52](Cl)=[O:53])=[O:44])[CH:33]=[C:34]([C:37]([CH3:40])([CH3:39])[CH3:38])[C:35]=1[OH:36])([CH3:29])([CH3:28])[CH3:27].S(=O)(=O)(O)O>C(OCC)C>[C:26]([C:30]1[CH:31]=[C:32]([CH2:41][CH2:42][C:43]([O:45][CH2:46][CH2:47][CH2:48][S:49][CH2:50][CH2:51][C:52]([O:15][CH2:14][CH2:13][CH2:12][C:7]2[CH:8]=[C:9]([CH3:11])[CH:10]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[C:6]=2[OH:16])=[O:53])=[O:44])[CH:33]=[C:34]([C:37]([CH3:38])([CH3:40])[CH3:39])[C:35]=1[OH:36])([CH3:27])([CH3:28])[CH3:29]

Participants

6

Reactant 4

HCID 949N,N-DimethylanilineHCID 1118Sulfuric AcidHCID 139809533-(3-Tert-butyl-2-hydroxy-5-methylphenyl)-1-propanolHCID 139809973-[3-[3-(3,5-Di-tert-butyl-4-hydroxyphenyl)propionyloxy]propylthio]propionyl chloride

Product 1

HCID 139809983-(3-Tert-butyl-2-hydroxy-5-methylphenyl)propyl 3-[3-(2-(3,5-di-tert-butyl-4-hydroxyphenyl)ethylcarbonyloxy]propylthio]propionateYield 67%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Into a 50 ml reactor were charged 3.40 g (15.29 mmol) of 3-(3-tert-butyl-2-hydroxy-5-methylphenyl)-1-propanol, 20 ml of diethyl ether and 1.94 g (16.00 mmol) of N,N-dimethylaniline. The atmosphere in the reactor was replaced with dry nitrogen. To the reactants was added dropwise 7.09 g (16.00 mmol) of 3-[3-[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionyloxy]propylthio]propionyl chloride. The reactants were heated and refluxed for 6 hours in the nitrogen stream. After the completion of the reaction, diethyl ether was added and the reaction product was neutralized with 10% sulfuric acid. After liquid separation, washing with saturated aqueous solution of sodium chloride and dehydration with anhydrous sodium sulfate, the organic solvent was removed under reduced pressure. After separation by silica gel chromatography (solvent: chloroform), 6.42 g (10.20 mmol) of the desired product was obtained. The yield was 67%. The physical properties of the product are shown below.

Workup

  1. temperatureThe reactants were heated
  2. temperaturerefluxed for 6 hours in the nitrogen stream
  3. additionwas added
  4. customAfter liquid separation
  5. washwashing with saturated aqueous solution of sodium chloride and dehydration with anhydrous sodium sulfate
  6. customthe organic solvent was removed under reduced pressure
  7. customAfter separation by silica gel chromatography (solvent: chloroform)

Sources & evidence

ORD record
ord-3fe4c93fd69b44559fd1c23ed54df325
Source dataset
uspto-grants-1987_09
Patent number
US04694102

Reaction notes

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