4-Hydroxybenzaldehyde → 4-(Methoxymethoxy)benzaldehyde

A suspension of 4-hydroxybenzaldehyde (55 g) and toluene-4-sulphonic acid (1.0 g) was stirred at reflux in a mixture of dichloromethane (500 ml) and dimethoxymethane (250 ml) under a Soxhlet extraction apparatus containing Type 3A molecular sieve (100 g). After 2 hours' reflux the molecular sieve was replaced with a fresh batch, and more toluene-4-sulphonic acid (1.0 g) was added to the reaction mixture. After 48 hour's reflux, the molecular sieve was changed again. After 66 hours' continuous reflux, the mixture was cooled and filtered to remove suspended solid. The filtrate was washed five times with 200 ml portions of N NaOH solution (i.e., until the NaOH solution was colourless after washing), and then it was washed with water and dried over anhydrous MgSO4. Removal of the solvent gave 4-(methoxymethoxy)benzaldehyde (47 g) as a light brown oil. This was used without further purification.

1. temperatureAfter 2 hours' reflux the molecular sieve
2. additionwas added to the reaction mixture
3. temperatureAfter 48 hour's reflux
4. temperaturethe mixture was cooled
5. filtrationfiltered
6. customto remove
7. washThe filtrate was washed five times with 200 ml portions of N NaOH solution (i.e.
8. washafter washing), and then it
9. washwas washed with water
10. dry with materialdried over anhydrous MgSO4
11. customRemoval of the solvent

ORD record

ord-9af9859bae8a4d248c365dc8602e6081

Source dataset

uspto-grants-1983_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04368253