Formaldehyde → 2,6-Di-tert-butyl-4-methylphenol

HRID 1249637Notes

Reaction equation

HRID 1249637 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].C=O.[CH2:18](N(CC)CC)C>[Ni].CO>[CH3:18][C:9]1[CH:10]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:6]([OH:15])=[C:7]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 8471TriethylamineHCID 314052,6-Di-tert-butylphenol

Product 1

HCID 314042,6-Di-tert-butyl-4-methylphenolYield 91.8%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Conditions

Temperature
127 °C

Procedure

A 2.5 liter shaker reactor was charged with 2,6-di-t-butylphenol (52 g, 0.25 m), formaldehyde (21 g of 37% aq. solution, 0.25 m), triethylamine (30 g, 0.3 m) and methyl alcohol (200 ml). The mixture was heated at 127° C. for 2 hrs. under a nitrogen blanket with agitation. The mixture was hydrogenated at 160° C. in the presence of nickel catalyst (5 g) and 300 psig of H2. Absorption of hydrogen ceased after 15 minutes. The product, after filtering to remove the catalyst, was distilled to recover methyl alcohol, triethylamine and crude DBPC which was distilled at 128° C./6-8 mm Hg to give 51 g (93 mole % yield) of DBPC. Analysis of DBPC by GC was 97% DBPC and 2.8% 2,6-di-t-butylphenol.

Workup

  1. customAbsorption of hydrogen
  2. filtrationThe product, after filtering
  3. customto remove the catalyst
  4. distillationwas distilled
  5. customto recover methyl alcohol, triethylamine and crude DBPC which
  6. distillationwas distilled at 128° C./6-8 mm Hg

Sources & evidence

ORD record
ord-c8b1848305aa44ecb95a538f2660b0fd
Source dataset
uspto-grants-1986_12
Patent number
US04633022

Reaction notes

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