Reaction #684957

Reaction equation

water

N,N-diisopropylethylamine

chloromethyl methyl ether

4-benzyloxy-2-hydroxybenzaldehyde

N,N-diisopropylethylamine

chloromethyl methyl ether

→

title compound

4-Benzyloxy-2-(methoxymethoxy)benzaldehyde

Solvents

tetrahydrofuran

Conditions

Workup

1. 1
   Temperatureheated
2. 2
   Temperatureunder reflux for 19 hours
3. 3
   workup.STIRRINGthe resulting mixture was stirred
4. 4
   Temperatureheated
5. 5
   Temperatureunder reflux for another 10 hours
6. 6
   Extractionthe reaction mixture was extracted with ethyl acetate
7. 7
   Washwashed with a saturated aqueous ammonium chloride solution and saturated brine
8. 8
   Dryingdried over anhydrous magnesium sulfate
9. 9
   Filtrationfiltered through silica gel and alumina
10. 10
    ConcentrationThe filtrate was concentrated under reduced pressure

Procedure

N,N-diisopropylethylamine (1.98 ml) and chloromethyl methyl ether (0.76 ml) were added to a solution of 4-benzyloxy-2-hydroxybenzaldehyde (2071 mg) in tetrahydrofuran (30 ml), and this reaction mixture was stirred and heated under reflux for 19 hours. N,N-diisopropylethylamine (2.7 ml) and chloromethyl methyl ether (1.04 ml) were further added, and the resulting mixture was stirred and heated under reflux for another 10 hours. After water was added, the reaction mixture was extracted with ethyl acetate, washed with a saturated aqueous ammonium chloride solution and saturated brine, dried over anhydrous magnesium sulfate, then filtered through silica gel and alumina. The filtrate was concentrated under reduced pressure to give the title compound (2470 mg). This compound was used in the following reaction without further purification.

Source