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

HRID 1798142Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11]C2CCCCO2)[CH:8]=[C:7]([CH3:18])[C:4]=1[CH:5]=[O:6]>CO>[OH:11][C:9]1[CH:8]=[C:7]([CH3:18])[C:4]([CH:5]=[O:6])=[C:3]([O:2][CH3:1])[CH:10]=1

Participants

Conditions

Temperature: 50 °C

Procedure

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).

Workup

customThe resin was removed by hot filtration
concentrationthe filtrate was concentrated to a yellow semi-solid
customThe residue was recrystallized from MeOH and hexanes

Sources & evidence

ORD record: ord-8ff27799a5054923883787024a39582c
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08343944B2

Reaction notes

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