Chemical Properties
white to light yellow crystal powde
Uses
4,5-Dimethoxy-2-nitrobenzyl alcohol (6-nitroveratryl alcohol) is suitable reagent used in the synthesis of 4,5-dimethoxy-2-nitrobenzyl methacrylate, a photolabile monomer and 2-(4-((4-(4,5-dimethoxy-2-nitrobenzyloxy)phenyl)cyclohexylidene)methyl)phenoxy)-
N,N-dimethylethanamine, a caged cyclofen-OH ligand.
It may be used in the synthesis of the following:
- 1-[[(chlorocarbonyl)oxy]methyl]-4,5-dimethoxy-2-nitrobenzene
- bis(4,5-dimethoxy-2-nitrophenyl)ethylene glycol, a photolabile protecting group
- optically-sensitive monomer
- nitroveratryl (NV) protected α-hydroxyacetic acid (αG) (NV-αG-OH), required in the preparation of nitroveratryl (NV) protected cyanomethyl (CM) ester of α-hydroxyacetic acid (αG) (NV-αG-CM)
- 4,5-dimethoxy-2-nitrobenzyl p-nitro-phenylcarbonate
- 6-nitroveratryloxycarbonyl chloride (NVOCCl), a reagent used in the protection of amino function in amino sugars
Uses
4,5-Dimethoxy-2-nitrobenzyl alcohol, is used as Reagent for the protection of alcohols, etc., as ethers which can be cleaved by photolysis involving intramolecular rearrangement to derivatives of o-nitrosobenzaldehyde, which are readily cleaved by hydrolysis. It is also used as photochemical protecting groups in organic synthesis. It is also used as a pharmaceutical intermediate.
General Description
4,5-Dimethoxy-2-nitrobenzyl alcohol (6-Nitroveratryl Alcohol) is 2-nitrobenzyl alcohol derivative. It has been reported to be one of the oxidation products of veratryl (3,4-dimethoxybenzyl) alcohol by lignin peroxidase (isolated from
Phanerochaete chrysosporium).
Synthesis
Step (a): sodium borohydride (7.6 g, 199 mmol) was slowly added to a solution of 4,5-dimethoxy-2-nitrobenzaldehyde (20.0 g, 95 mmol) in a solvent mixture of methanol/dichloromethane (800 mL; 3:1) at 0 °C. The reaction mixture was stirred at room temperature overnight before the reaction was quenched by the addition of water. The organic layer was separated, washed sequentially with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. Purification by silica gel column chromatography (dichloromethane as eluent) afforded the pure product 4,5-dimethoxy-2-nitrobenzyl alcohol (19.7 g, 92 mmol) as a yellow solid in 99% yield.
References
[1] European Journal of Medicinal Chemistry, 2016, vol. 115, p. 453 - 462
[2] Journal of Organic Chemistry, 1998, vol. 63, # 8, p. 2434 - 2441
[3] Tetrahedron, 1997, vol. 53, # 39, p. 13449 - 13472
[4] Journal of Organic Chemistry, 2002, vol. 67, # 16, p. 5567 - 5577
[5] Chemical Communications, 2017, vol. 53, # 68, p. 9470 - 9473
