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

HRID 2254128Notes

Reaction equation

HRID 2254128 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>C(Cl)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

5

Reactant 3

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

Product 1

HCID 15027766HCID 15027766, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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 CH2Cl2 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 1N 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 1N 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-b5bc1b7ed7d4415faddd9d60eb4b4c69
Source dataset
uspto-grants-1993_08
Patent number
US05234939

Reaction notes

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