Water → 3,5-Di-tert-butylsalicylaldehyde

HRID 1110158Notes

Reaction equation

HRID 1110158 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[CH:7][C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2].[CH2:16]1N2CN3CN(C2)CN1C3.[OH2:26]>C(O)(=O)C>[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[C:7]([CH:16]=[O:26])[C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 4101HexamethylenetetramineHCID 73112,4-Di-tert-butylphenol

Product 1

HCID 6880233,5-Di-tert-butylsalicylaldehydeYield 46.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 10.42 g (50 mmol) of 2,4-di-tert-butylphenol and 21.03 g 150 mmol) of hexamethylenetetramine (HMT) in 50 mL of glacial acetic acid was heated at 130° C. with stirring for 2 hours. Twenty-five mL of water was then added and the resulting mixture was refluxed for 0.5 h. After cooling and workup as in Example 1, 5.5 g of 3,5-di-tert-butylsalicylaldehyde was obtained (46.9% yield).

Workup

  1. temperaturethe resulting mixture was refluxed for 0.5 h
  2. temperatureAfter cooling and workup as in Example 1

Sources & evidence

ORD record
ord-28c1b48bffa24dd2b63c541655a8f899
Source dataset
uspto-grants-1994_06
Patent number
US05324860

Reaction notes

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