4-Hydroxybenzaldehyde → 4-(Methoxymethoxy)benzaldehyde

Temperatur

0 °C

A solution of 4-hydroxybenzaldehyde (118.20 g, 0.968 mol) in dichloromethane (1.1 L) was stirred mechanically and cooled to 0° C., under argon. N,N-diisopropylethylamine (337.2 ml) was added to the reaction, and the mixture was stirred until homogenous. Chloromethyl methyl ether (101.30 g, 1.94 mol) was added dropwise, maintaining reaction temperature below 10° C. After the addition, the solution was warmed to room temperature, then stirred for 1 hour. The reaction was quenched with water (500 ml), and the aqueous phase was separated from the organic phase. The organic layer was washed with water, 5% glacial acetic acid, and saturated aqueous NaCl. The solution was dried with sodium sulfate, filtered, and rotary evaporated, yielding 170 g of pure product.

1. temperaturemaintaining
2. customreaction temperature below 10° C
3. additionAfter the addition
4. temperaturethe solution was warmed to room temperature
5. stirringstirred for 1 hour
6. customThe reaction was quenched with water (500 ml)
7. customthe aqueous phase was separated from the organic phase
8. washThe organic layer was washed with water, 5% glacial acetic acid, and saturated aqueous NaCl
9. dry with materialThe solution was dried with sodium sulfate
10. filtrationfiltered

ORD-Eintrag

ord-33e9518e3ee64994824aac22f56a4c8e

Quelldatensatz

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08846735B2