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

HRID 436540Notes

Reaction equation

HRID 436540 reaction equation
O.[C:2]([O-])(=[O:4])C.[NH4+].C=O.[C:9]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:14]=1[OH:23])([CH3:12])([CH3:11])[CH3:10]>C(O)(=O)C>[C:19]([C:15]1[CH:16]=[C:17]([CH:18]=[C:13]([C:9]([CH3:12])([CH3:11])[CH3:10])[C:14]=1[OH:23])[CH:2]=[O:4])([CH3:22])([CH3:21])[CH3:20]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 962WaterHCID 314052,6-Di-tert-butylphenolHCID 517165Ammonium Acetate

Product 1

HCID 732193,5-Di-tert-butyl-4-hydroxybenzaldehydeYield 67.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A 500 ml reaction flask fitted with a mechanical stirrer, heating mantle, thermometer and water-cooled condenser was charged with 200 ml of glacial acetic acid, and 61.7 g (0.8 mole) of ammonium acetate. To the stirred mixture there were slowly added 97 g of 37% formalin (1.2 moles of formaldehyde) and 20.6 g (0.1 mole) of 2,6-ditert.-butylphenol. The reaction flask was equipped with a take-off head to remove the methanol which is present in commercially available formalin. The mixture was refluxed (107°-9°) for 6 hours. After cooling to ambient temperature, the mixture was poured on a vacuum filter and the product cake was washed with water. After drying, there was obtained 15.8 g of crystalline 3,5-ditert.butyl-4-hydroxybenzaldehyde, m.p. 184°-86° (67.5%).

Workup

  1. customA 500 ml reaction flask
  2. customfitted with a mechanical stirrer
  3. temperatureheating mantle
  4. customThe reaction flask was equipped with a take-off head
  5. customto remove the methanol which
  6. temperatureThe mixture was refluxed (107°-9°) for 6 hours
  7. additionthe mixture was poured on a vacuum
  8. filtrationfilter
  9. washthe product cake was washed with water
  10. customAfter drying

Sources & evidence

ORD record
ord-8b97c6b4a1ec4607a2698c4e79bff7cf
Source dataset
uspto-grants-1977_02
Patent number
US04009210

Reaction notes

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