3-Hydroxybenzaldehyde → 3-(Methoxymethoxy)benzaldehyde

A solution of 100 g of 3-hydroxybenzaldehyde and 214 ml of N-ethyldiisopropylamine in 800 ml of dichloromethane was ice-cooled and a solution of 68.4 ml of chloromethyl methyl ether in 200 ml of dichloromethane was added dropwise. After stirring for one hour, an ice bath was removed and the mixture was continuously stirred at room temperature overnight. The reaction solution was washed in turn with an aqueous 10% sodium hydroxide solution and 10% citric acid and dried over magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was distilled off under reduced pressure to obtain 81.3 g of the desired compound as a colorless oily substance. Boiling point: 125 to 127° C./10 mmHg

1. temperaturecooled
2. customan ice bath was removed
3. stirringthe mixture was continuously stirred at room temperature overnight
4. washThe reaction solution was washed in turn with an aqueous 10% sodium hydroxide solution and 10% citric acid
5. dry with materialdried over magnesium sulfate
6. customthe solvent was evaporated under reduced pressure
7. distillationThe residue was distilled off under reduced pressure

ORD record

ord-080f6b4ca5bc4f878cbc855e43232ca9

Source dataset

uspto-grants-2007_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07205302B2