Water → 1-Ethyl-2-(3,5-di-tert.butyl-4-hydroxyphenyl)-1-nitroethane

HRID 1729756Notes

Reaction equation

HRID 1729756 reaction equation
[Cl-].[C:2]([C:6]1[CH:7]=[C:8]([CH:16]=[C:17]([C:20]([CH3:23])([CH3:22])[CH3:21])[C:18]=1[OH:19])[CH2:9][N+]1C=CC=CC=1)([CH3:5])([CH3:4])[CH3:3].[OH-].[Na+].[N+:26]([CH2:29][CH2:30][CH3:31])([O-:28])=[O:27].O>C(O)C>[CH2:30]([CH:29]([N+:26]([O-:28])=[O:27])[CH2:9][C:8]1[CH:16]=[C:17]([C:20]([CH3:21])([CH3:23])[CH3:22])[C:18]([OH:19])=[C:6]([C:2]([CH3:4])([CH3:3])[CH3:5])[CH:7]=1)[CH3:31]

Participants

6

Reactant 4

HCID 962WaterHCID 79031-NitropropaneHCID 14798Sodium HydroxideHCID 104969033,5-Di-t-butyl-4-hydroxy-benzylpyridinium chloride

Product 1

HCID 203223811-Ethyl-2-(3,5-di-tert.butyl-4-hydroxyphenyl)-1-nitroethaneYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 16.7 grams of 3,5-di-tert.butyl-4-hydroxybenzylpyridinium chloride in 50 milliliters of ethanol was added dropwise in 15 minutes to a slurry of 2.0 grams of sodium hydroxide and 13.4 grams of 1-nitropropane (200% excess) in 50 milliliters of ethanol. The reaction mixture as stirred for 3 hours and was then poured into 600 milliliters of water. The oil which precipitated was separated by extraction with hexane. The extract was evaporated to give 15.0 grams (98% of theory) of 1-ethyl-2-(3,5-di-tert.butyl-4-hydroxyphenyl)-1-nitroethane which melted at 55°-60° C.

Workup

  1. customThe oil which precipitated
  2. customwas separated by extraction with hexane
  3. customThe extract was evaporated

Sources & evidence

ORD record
ord-b8898968e2e446f3a77f5ffb442e79bf
Source dataset
uspto-grants-1976_11
Patent number
US03989738

Reaction notes

Loading…