2-Nitropropane → 2,6-Di-t-butyl-4-(2-methyl-2-nitropropyl)phenol

HRID 435930Notes

Reaction equation

HRID 435930 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2].[CH2:16]=O.[OH-].[K+].[N+:20]([CH:23]([CH3:25])[CH3:24])([O-:22])=[O:21]>CO>[C:11]([C:7]1[CH:8]=[C:9]([CH2:24][C:23]([CH3:16])([N+:20]([O-:22])=[O:21])[CH3:25])[CH:10]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:6]=1[OH:15])([CH3:14])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 3982-NitropropaneHCID 712FormaldehydeHCID 14797Potassium HydroxideHCID 314052,6-Di-tert-butylphenol

Product 1

HCID 203223902,6-Di-t-butyl-4-(2-methyl-2-nitropropyl)phenol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2,6-di-t-butylphenol, 20.6 g, in 100 ml of stirred methanol containing 16.2 g of 37% aqueous formaldehyde (excess) was treated with a freshly prepared solution of 5.6 g of potassium hydroxide and 8.9 g of 2-nitropropane and heated under nitrogen for 21/2 hours. Upon cooling, 19.8 g of product, mp 101°-4° C., was obtained in two crops. Recrystallization from methanol afforded product melting 103.5°-105.5° C.

Workup

  1. temperatureheated under nitrogen for 21/2 hours
  2. temperatureUpon cooling

Sources & evidence

ORD record
ord-178e1b7870464d5a8ee55cf96cddd3e1
Source dataset
uspto-grants-1977_02
Patent number
US04007159

Reaction notes

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