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

HRID 1533891Notes

Reaction equation

HRID 1533891 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-d612b06489404e7eba9f080f533b74bb
Source dataset
uspto-grants-1992_02
Patent number
US05086064

Reaction notes

Loading…