4-methoxymethoxy-benzaldehyde synthesis
- Product Name:4-methoxymethoxy-benzaldehyde
- CAS Number:6515-21-5
- Molecular formula:C9H10O3
- Molecular Weight:166.17
Yield:6515-21-5 100%
Reaction Conditions:
with potassium carbonate in acetonitrile at 20; for 3 h;
Steps:
2. Preparation of benzaldehydes (1u, 1v and 1w) 4-(methoxymethoxy)benzaldehyde (1w)
A solution of 4-hydroxybenzaldehyde (1t) (1.0 eq, 2.46 mmol), bromomethyl methyl ether [CAS NO. 592-55-2] (2.0 eq, 4.92 mmol) and potassium carbonate [CAS NO. 584-08-7] (2.5 eq, 6.15 mmol) in acetonitrile (ACN, 20 mL) in a 50 mL round bottom flask. The mixture was stirred at room temperature for 3 hours. The reaction mixture was washed with water (3x20 mL) and the organic portion was extracted with EtOAc (3x20 mL). The organic layer was eliminated water by Na2SO4. After filtration and removal of the solvent under reduced pressure, the crude product was purified by silica gel column chromatography (3:1 of Hexane:EtOAc) to afford 1w in 264.4 mg, 1.59 mmol, 65% yield as a colorless oil: 1H-NMR (500 MHz, CDCl3): δ (ppm) 9.87 (s, 1H), 7.81 (d, J = 8.84 Hz, 2H), 7.12 (d, J = 8.75 Hz, 2H), 5.23 (s, 2H), 3.47 (s, 3H). 13C-NMR (125 MHz, CDCl3): δ (ppm) 191.0, 162.3, 132.0, 130.8, 116.4, 94.2, 56.5. FT-IR (cm-1): 3080, 2960, 2900, 2832, 2740, 1697, 1603, 1512, 1322, 1245, 1160, 1086, 983.
References:
Rerkrachaneekorn, Tanawat;Tankam, Theeranon;Sukwattanasinitt, Mongkol;Wacharasindhu, Sumrit [Tetrahedron Letters,2021,vol. 70,art. no. 153017] Location in patent:supporting information
