4-Hydroxybenzaldehyde → 4-(Methoxymethoxy)benzaldehyde

Participants

Reaction Steps

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.

Provenance & Evidence