3,5-Di-tert-butyl-4-hydroxybenzaldehyde → HCID 15027766, compound

HRID 2254108Notes

Reaction equation

HRID 2254108 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:12]=1[OH:13])[CH:8]=[O:9])([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.[CH3:27][O:28][CH2:29][CH2:30][O:31][CH2:32]Cl>>[CH3:15][C:14]([C:11]1[CH:10]=[C:7]([CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:12]=1[O:13][CH2:27][O:28][CH2:29][CH2:30][O:31][CH3:32])[CH:8]=[O:9])([CH3:17])[CH3:16]

Participants

4

Reactant 3

HCID 732193,5-Di-tert-butyl-4-hydroxybenzaldehydeHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 81531Diisopropylethylamine

Product 1

HCID 15027766HCID 15027766, compoundYield 76%

Procedure

A mixture of 11.7 g (0.05 mole) of 3,5-di-tert-butyl 4-hydroxybenzaldehyde and 19.4 g (0.15 mole) of diisopropylethylamine in 150 mL of CH1C12 is treated with 18.7 g (0.15 mole) of 2-methoxyethoxymethyl chloride (MEM-Cl) and the resulting solution is heated under reflux for 48 hours and evaporated to dryness. The residue is taken up in CH2Cl2, washed with IN HCl and brine, and dried with MgSO4. The solution is evaporated and the residue is filtered through flash grade silica gel, washing with 1:1 CH2Cl2 /n-hexane. Evaporation gives a tan oil, 12.2 g of 3,5-bis(1,1-dimethylethyl)-4-[(2-methoxyethoxy)methoxy]benzaldehyde (76%) which is used without further purification.

Workup

  1. temperaturethe resulting solution is heated
  2. temperatureunder reflux for 48 hours
  3. customevaporated to dryness
  4. washwashed with IN HCl and brine
  5. dry with materialdried with MgSO4
  6. customThe solution is evaporated
  7. filtrationthe residue is filtered through flash grade silica gel
  8. washwashing with 1:1 CH2Cl2 /n-hexane
  9. customEvaporation

Sources & evidence

ORD record
ord-390cfc28a82c47959fa9253ae4a57be8
Source dataset
uspto-grants-1993_08
Patent number
US05234937

Reaction notes

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