Water → 3,5-Di-tert-butyl-4-hydroxybenzaldehyde

HRID 1511178Notes

Reaction equation

HRID 1511178 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]1N2CN3CN(C2)CN1C3.[OH2:26]>C(O)(=O)C>[C:11]([C:7]1[CH:8]=[C:9]([CH:10]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:6]=1[OH:15])[CH:16]=[O:26])([CH3:14])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 962WaterHCID 4101HexamethylenetetramineHCID 314052,6-Di-tert-butylphenol

Product 1

HCID 732193,5-Di-tert-butyl-4-hydroxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2,6-di-tert-butylphenol was dissolved in glacial acetic acid. Subsequently, urotropin and water were added, and the reaction mixture heated at not more than 2° C. below the reflux temperature for 4 to 5 hours. The precipitated product was filtered off and washed with water and methanol, and dried on a rotary evaporator. The molar ratios of the reactants used and also the determined yields of 3,5-di-tert-butyl-4-hydroxybenzaldehyde, based on 2,6-di-tert-butylphenol, are shown in Table 4.

Workup

  1. temperaturethe reaction mixture heated at not more than 2° C. below the reflux temperature for 4 to 5 hours
  2. filtrationThe precipitated product was filtered off
  3. washwashed with water and methanol
  4. customdried on a rotary evaporator

Sources & evidence

ORD record
ord-95ebbb52671e4d0dbde64ecec9231898
Source dataset
uspto-grants-2012_07
Patent number
US08212081B2

Reaction notes

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