Ethylene Glycol → 3,5-Bis(tert-butyl)benzaldehyde

HRID 1872923Notes

Reaction equation

HRID 1872923 reaction equation
B(O)(O)O.C1N2CN3CN(C2)CN1C3.[CH3:15][C:16]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([CH3:28])([CH3:27])[CH3:26])[C:20]=1O)([CH3:18])[CH3:17].OS(O)(=O)=O.C(O)[CH2:36][OH:37]>>[CH3:15][C:16]([C:19]1[CH:24]=[C:23]([CH:22]=[C:21]([C:25]([CH3:28])([CH3:27])[CH3:26])[CH:20]=1)[CH:36]=[O:37])([CH3:18])[CH3:17]

Participants

6

Reactant 5

HCID 174Ethylene GlycolHCID 1118Sulfuric AcidHCID 4101HexamethylenetetramineHCID 7628Boric AcidHCID 314052,6-Di-tert-butylphenol

Product 1

HCID 12682533,5-Bis(tert-butyl)benzaldehyde

Conditions

Temperature
149 °C

Procedure

3.5 g of boric acid was heated in 150 ml of ethylene glycol at 150° C. for 30 minutes, in a 500 cc flask equipped with a reflux condenser. 25 g of hexamethylenetetramine and 21 g of 2,6-bis(1,1-dimethylethyl)phenol were then added and the solution maintained at 148-150° C. for 15 minutes. After cooling to 125° C. at which stage the first crystals appeared, 150 ml of H2SO4 (30%0 was added and stirring was continued for another 30 minutes. The resulting slurry was filtered and washed with warm water. After drying, 22 g of 3,5-bis(1,1-dimethylethyl)benzaldehyde was obtained.

Workup

  1. customequipped with a reflux condenser
  2. temperatureAfter cooling to 125° C. at which stage the first crystals
  3. filtrationThe resulting slurry was filtered
  4. washwashed with warm water
  5. customAfter drying

Sources & evidence

ORD record
ord-c5d9cc46277f4d38b45f49b414d69111
Source dataset
uspto-grants-2000_08
Patent number
US06111047

Reaction notes

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