2-Methoxy-4-(2-tetrahydropyranyl)oxy-6-methylbenzaldehyde → 4-Hydroxy-2-methoxy-6-methylbenzaldehyde

Participants

Reaction Conditions

Reaction Steps

Crude 2-methoxy-6-methyl-4-(tetrahydro-pyran-2-yloxy)-benzaldehyde from the above step was diluted with MeOH (30 mL), then treated with Amberlyst® 15 (0.10 g). The suspension was heated at 50° C. for 1 h. The resin was removed by hot filtration and the filtrate was concentrated to a yellow semi-solid. The residue was recrystallized from MeOH and hexanes to give 4-hydroxy-2-methoxy-6-methyl-benzaldehyde (4.16 g, 78% over 2 steps), as a yellow solid. 1H NMR (400 MHz, CDCl3) δ 10.47 (s, 1H), 6.32 (s, 1H), 6.25 (s, 1H), 5.49 (br s, 1H), 3.87 (s, 3H), 2.56 (s, 3H).

Provenance & Evidence