Salicylaldehyde → 3,5-Di-tert-butyl-4-(methoxymethoxy)benzaldehyde

HRID 890627Notes

Reaction equation

HRID 890627 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(CC)C(C)C)(C)C.Cl[CH2:28][O:29][CH2:30]OCOCCl.OC1C=CC=CC=1C=O>ClCCCl>[CH3:28][O:29][CH2:30][O:13][C:12]1[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6][C:7]([CH:8]=[O:9])=[CH:10][C:11]=1[C:14]([CH3:17])([CH3:16])[CH3:15]

Participants

6

Reactant 4

HCID 6998SalicylaldehydeHCID 732193,5-Di-tert-butyl-4-hydroxybenzaldehydeHCID 81531DiisopropylethylamineHCID 22246685HCID 22246685, compound

Product 1

HCID 106363293,5-Di-tert-butyl-4-(methoxymethoxy)benzaldehydeYield 100%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 3,5-di-tert-butyl-4-hydroxybenzaldehyde (10 g, 40 mmol) in 1,2-dichloroethane (200 mL) was added N,N-diisopropylethylamine (6.97 mL, 40 mmol) and the solution was stirred for 1 h at room temperature. Chloromethoxymethyl ether (3.77 mL, 50 mmol) was added and the reaction mixture was stirred for 1 h at room temperature and then refluxed for 16 h until no more hydroxybenzaldehyde was detected by TLC (Rf=0.78 for product and 0.70 for starting, material using 1:1 hexanes/EtOAc). The reaction mixture was cooled to room temperature and washed with water. The organic layer was concentrated and the residue applied to a silica gel column and eluted with mixture of pentane/EtOAc. The title compound was isolated in 100% yield as a brown oil.

Workup

  1. stirringthe reaction mixture was stirred for 1 h at room temperature
  2. temperatureThe reaction mixture was cooled to room temperature
  3. washwashed with water
  4. concentrationThe organic layer was concentrated
  5. washeluted with mixture of pentane/EtOAc

Sources & evidence

ORD record
ord-3f49a10250914a46ac3c162ae647fb74
Source dataset
uspto-grants-2006_02
Patent number
US06998419B2

Reaction notes

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