Acetic Acid → 1,3-Bis(3,5-di-t-butyl-4-hydroxyphenyl)-2-nitropropane

HRID 2398204Notes

Reaction equation

HRID 2398204 reaction equation
[OH-].[K+].[N+:3]([CH3:6])([O-:5])=[O:4].[C:7]([C:11]1[CH:16]=[C:15]([CH2:17]OC)[CH:14]=[C:13]([C:20]([CH3:23])([CH3:22])[CH3:21])[C:12]=1[OH:24])([CH3:10])([CH3:9])[CH3:8].[C:25]([OH:28])(=O)[CH3:26]>CO>[C:7]([C:11]1[CH:16]=[C:15]([CH2:17][CH:6]([N+:3]([O-:5])=[O:4])[CH2:17][C:15]2[CH:16]=[C:26]([C:7]([CH3:8])([CH3:9])[CH3:10])[C:25]([OH:28])=[C:13]([C:20]([CH3:23])([CH3:21])[CH3:22])[CH:14]=2)[CH:14]=[C:13]([C:20]([CH3:22])([CH3:21])[CH3:23])[C:12]=1[OH:24])([CH3:9])([CH3:10])[CH3:8]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6375NitromethaneHCID 69112,6-Di-tert-butyl-4-(methoxymethyl)phenolHCID 14797Potassium Hydroxide

Product 1

HCID 214348841,3-Bis(3,5-di-t-butyl-4-hydroxyphenyl)-2-nitropropane

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 14.5 g (0.22 mole) of 85% potassium hydroxide in 300 ml of methanol was added in a stream of nitrogen to exclude air 13.4 g (0.22 mole) of nitromethane and 50.0 g (0.2 mole) of 2.6-di-t-butyl-4-methoxymethylphenol. The magenta solution was stirred for one hour at reflux, with exclusion of air. After cooling somewhat, the solution was neutralized with 13 ml of acetic acid and chilled. A thick paste formed which was filtered, washed and dried. The resulting tan powder (48.1 g, mp 152°-154° C) was recrystallized from 500 ml of heptane, after filtering insoluble matter (10.4 g). The yield of tan crystals was 32.3 g, mp 161°-165° C.

Workup

  1. temperatureat reflux, with exclusion of air
  2. temperatureAfter cooling somewhat
  3. temperaturechilled
  4. customA thick paste formed which
  5. filtrationwas filtered
  6. washwashed
  7. customdried
  8. customThe resulting tan powder (48.1 g, mp 152°-154° C) was recrystallized from 500 ml of heptane
  9. filtrationafter filtering insoluble matter (10.4 g)

Sources & evidence

ORD record
ord-b1869032e2224ba19f96bdf5c90be1e5
Source dataset
uspto-grants-1977_05
Patent number
US04024186

Reaction notes

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