Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → 4-Hydroxy-2-methoxymethoxy-6-methyl-benzaldehyde

HRID 1798150Notes

Reaction equation

HRID 1798150 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:12]=[C:11]([O:13]C2CCCCO2)[CH:10]=[C:9]([CH3:20])[C:6]=1[CH:7]=[O:8].CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>CO>[OH:13][C:11]1[CH:10]=[C:9]([CH3:20])[C:6]([CH:7]=[O:8])=[C:5]([O:4][CH2:3][O:2][CH3:1])[CH:12]=1

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 866539772-Methoxymethoxy-6-methyl-4-(tetrahydro-pyran-2-yloxy)-benzaldehyde

Product 1

HCID 582925684-Hydroxy-2-methoxymethoxy-6-methyl-benzaldehydeYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-methoxymethoxy-6-methyl-4-(tetrahydro-pyran-2-yloxy)-benzaldehyde (9.8 g, 34.9 mmol) in MeOH (100 mL) was added PPTS (2.19 g, 8.7 mmol). The reaction mixture was stirred at room temperature for 12 hours then concentrated in vacuo. The residue was purified by silica gel flash column chromatography (hexane:EtOAc 80:20) to give 4-hydroxy-2-methoxymethoxy-6-methyl-benzaldehyde (5.4 g, 79%). 1H NMR (400 MHz, CDCl3): δ 10.47 (s, 1H), 6.65 (s, 1H), 6.57 (d, J=2.0 Hz, 1H), 6.37 (s, 1H), 5.24 (s, 2H), 3.50 (s, 3H), 2.56 (s, 3H). MS (ESI) m/z=195 [M−H]−.

Workup

  1. concentrationthen concentrated in vacuo
  2. customThe residue was purified by silica gel flash column chromatography (hexane:EtOAc 80:20)

Sources & evidence

ORD record
ord-e3a32a6e20c94eb9b1bdc880acba2aec
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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