2-Methoxy-5-methylbenzaldehyde

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2-Methoxy-5-methylbenzaldehyde Basic information
Product Name:2-Methoxy-5-methylbenzaldehyde
Synonyms:5-Methyl-2-methoxybenzaldehyde;Benzaldehyde, 2-methoxy-5-methyl-
CAS:7083-19-4
MF:C9H10O2
MW:150.17
EINECS:
Product Categories:
Mol File:7083-19-4.mol
2-Methoxy-5-methylbenzaldehyde Structure
2-Methoxy-5-methylbenzaldehyde Chemical Properties
density 1.08
storage temp. under inert gas (nitrogen or Argon) at 2-8°C
AppearanceColorless to light yellow Liquid
Safety Information
HazardClass IRRITANT
MSDS Information
2-Methoxy-5-methylbenzaldehyde Usage And Synthesis
Synthesis
5-Methylsalicylaldehyde

613-84-3

Iodomethane

74-88-4

2-METHOXY-5-METHYLBENZALDEHYDE

7083-19-4

Step 1: Suspend 5-methylsalicylaldehyde (2-hydroxy-5-methylbenzaldehyde, CAS No. 613-84-3) in a solvent mixture of 5 mL dichloromethane and 5 mL water. 1.47 mL (4.4 mmol, 3 eq.) of 1 N sodium hydroxide solution and 1.52 g (2.94 mmol, 2 eq.) of 50% aqueous tetrabutylammonium hydroxide were added sequentially, followed by iodomethane (457 μL, 5 eq.). The reaction mixture was stirred at room temperature for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane three times, the organic phases were combined, washed with saturated brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by silica gel fast column chromatography (eluent: cyclohexane/ethyl acetate, 9/1, v/v) to afford 215 mg (97% yield) of the target compound 2-methoxy-5-methylbenzaldehyde.

References[1] Canadian Journal of Chemistry, 2012, vol. 90, # 11, p. 965 - 974
[2] Journal of Medicinal Chemistry, 2002, vol. 45, # 19, p. 4188 - 4201
[3] Patent: WO2010/66847, 2010, A1. Location in patent: Page/Page column 70
[4] Indian Journal of Chemistry - Section B Organic Chemistry Including Medicinal Chemistry, 1990, vol. 29, # 9, p. 876 - 878
[5] Beilstein Journal of Organic Chemistry, 2018, vol. 14, p. 734 - 746
2-Methoxy-5-methylbenzaldehyde Preparation Products And Raw materials
Raw materials5-Methylsalicylaldehyde-->Iodomethane-->Dichloromethane-->Sodium hydroxide-->Tetrabutylammonium hydroxide-->Water
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