ChemicalBook CAS DataBase List 3-methoxy-4-(methoxymethoxy)benzaldehyde

3-methoxy-4-(methoxymethoxy)benzaldehyde synthesis

6synthesis methods

Product Name:3-methoxy-4-(methoxymethoxy)benzaldehyde
CAS Number:5533-00-6
Molecular formula:C10H12O4
Molecular Weight:196.1999

13057-17-5 Synthesis

13057-17-5
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121-33-5 Synthesis

121-33-5
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3-methoxy-4-(methoxymethoxy)benzaldehyde

5533-00-6
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Yield:5533-00-6 98%

Reaction Conditions:

with N-ethyl-N,N-diisopropylamine in dichloromethane; for 0.75 h;Inert atmosphere;Cooling with ice;

Steps:

4.14 Preparation of 3-methoxy-4-methoxymethoxybenzaldehyde 7e

An ice cooled stirred solution of 3-methoxy-4-hydroxybenzaldehyde (9.13 g, 60 mmol) and N,N-diisopropylethylamine (21 mL, 120 mmol) in anhydrous methylene chloride (400 mL) under nitrogen was treated dropwise with bromomethyl methyl ether (6.0 mL, 66 mmol corrected for 90%) and stirred on an ice bath for 45 min. Aqueous sodium hydroxide (1 M, 150 mL) was added and the mixture stirred for a few minutes and separated. The aqueous solution was extracted with dichloromethane (100 mL) and the combined organic solution washed with water (200 mL), dried (Na₂SO₄), and concentrated in vacuo. The residue was dissolved in minimum dichloromethane and loaded onto a silica gel column and eluted with 1.5% ethyl acetate/dichloromethane to afford 3-methoxy-4-methoxymethoxybenzaldehyde (11.56 g, 98%) as a colorless oil: LC/MS m/z 197 [M+H]; ¹H NMR (CDCl₃, 400 MHz) δ 3.52 (s, 3H), 3.95 (s, 3H), 5.32 (s, 2H), 7.27 (d, J = 8.2, 1H), 7.41-7.45 (m, 2H), 9.87 (s, 1H); ¹³C NMR (CDCl₃, 100 MHz) δ 56.2, 56.6, 95.2, 109.8, 115.0, 126.4, 131.3, 150.3, 152.2, 191.0. Anal. Calcd for C₁₀H₁₂O₄: C, 61.22; H, 6.16. Found: C, 60.94; H, 6.23.

References:

Zhang, Mingbao;Erik Jagdmann Jr.;Van Zandt, Michael;Beckett, Paul;Schroeter, Hagen [Tetrahedron Asymmetry,2013,vol. 24,# 7,p. 362 - 373]

121-33-5 Synthesis

121-33-5
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$9.00/1g