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

HRID 436541Notes

Reaction equation

HRID 436541 reaction equation
[C:1]([O-])(=[O:3])C.[NH4+].C=O.[C:8]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:13]=1[OH:22])([CH3:11])([CH3:10])[CH3:9]>O.C(O)(=O)C>[C:18]([C:14]1[CH:15]=[C:16]([CH:17]=[C:12]([C:8]([CH3:11])([CH3:10])[CH3:9])[C:13]=1[OH:22])[CH:1]=[O:3])([CH3:21])([CH3:20])[CH3:19]

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 314052,6-Di-tert-butylphenolHCID 517165Ammonium Acetate

Product 1

HCID 732193,5-Di-tert-butyl-4-hydroxybenzaldehydeYield 58%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

A 500 ml reaction flask fitted with a mechanical stirrer, heating mantle, thermometer and water-cooled condenser was charged with 166 ml of glacial acetic acid and 34 ml of water. To the stirred solution were added 61.7 g (0.8 mole) of ammonium acetate, 12 g of paraformaldehyde (0.4 mole equivalent of formaldehyde) and 20.6 g (0.1 mole) of 2,6-ditert.butylphenol. The mixture was refluxed (111°-12°) for 6 hours. After cooling to ambient temperature, the mixture was poured on a vacuum filter and the cake was washed with water. After drying, there was obtained 13.6 g (58%) of impure 3,5-ditert.butyl-4-hydroxybenzaldehyde, m.p. 174°-80°. Following recrystallization from 2-propanol, the yellow crystalline product melted at 188°-90°.

Workup

  1. customA 500 ml reaction flask
  2. customfitted with a mechanical stirrer
  3. temperatureheating mantle
  4. temperatureThe mixture was refluxed (111°-12°) for 6 hours
  5. additionthe mixture was poured on a vacuum
  6. filtrationfilter
  7. washthe cake was washed with water
  8. customAfter drying

Sources & evidence

ORD record
ord-4326bda399d5465bad9389952095eda4
Source dataset
uspto-grants-1977_02
Patent number
US04009210

Reaction notes

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