3,5-Di-tert-butyl-4-methoxybenzaldehyde Chemical Properties

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

3,5-Di-tert-butyl-4-methoxybenzaldehyde Usage And Synthesis

Synthesis

General procedure for the synthesis of 3,5-di-tert-butyl-4-hydroxybenzaldehyde from 3,5-di-tert-butyl-4-methoxybenzaldehyde and iodomethane: (1) Sodium hydride (NaH, 1.27 g, 53 mmol) was slowly added to a solution of 3,5-di-tert-butyl-4-hydroxybenzaldehyde (5 g, 21 mmol) dissolved in anhydrous tetrahydrofuran (THF, 22.5 ml) under the protection of nitrogen gas, keeping the reaction temperature at 0 °C. After the reaction mixture was removed from the cooling bath, stirring was continued for 30 minutes. (2) Subsequently, methyl iodide (CH3I, 5.2 ml, 84 mmol) dissolved in anhydrous THF (9 ml) was added to the reaction mixture and the mixture was refluxed for 12 hours. (3) After completion of the reaction, the reaction was quenched with methanol (MeOH) and then extracted with dichloromethane (CH2Cl2). (4) The organic layers were combined, concentrated and purified by column chromatography using ethyl acetate: hexane = 1:7 as eluent. (5) The final yellow liquid product 3,5-di-tert-butyl-4-methoxybenzaldehyde (4.5 g, 87% yield) was obtained. 1H NMR (CDCl3,400MHz) δ 9.91 (s, 1H), 7.79 (s, 2H), 3.73 (s, 3H), 1.46 (s, 18H).

References

[1] Patent: US9691555, 2017, B2. Location in patent: Page/Page column 29
[2] Bioorganic and Medicinal Chemistry, 2002, vol. 10, # 10, p. 3257 - 3265
[3] New Journal of Chemistry, 2006, vol. 30, # 4, p. 583 - 591

3,5-Di-tert-butyl-4-methoxybenzaldehyde(74684-38-1)Related Product Information

• FMOC-(R)-3-AMINO-4-(2,4-DICHLORO-PHENYL)-BUTYRIC ACID
• BOC-(S)-3-AMINO-4-(2,4-DICHLORO-PHENYL)-BUTYRIC ACID
• FMOC-(S)-3-AMINO-4-(2,4-DICHLORO-PHENYL)-BUTYRIC ACID
• BOC-(R)-3-AMINO-4-(2,4-DICHLORO-PHENYL)-BUTYRIC ACID
• (S)-3-AMINO-4-(2,4-DICHLOROPHENYL)BUTANOIC ACID HYDROCHLORIDE
• L-689,560
• 4-(2,4-DICHLORO-PHENYL)-2,4-DIOXO-BUTYRIC ACID METHYL ESTER
• 4-(2,4-DICHLORO-PHENYL)-2,4-DIOXO-BUTYRIC ACID
• (R)-3-AMINO-4-(2,4-DICHLOROPHENYL)BUTANOIC ACID HYDROCHLORIDE
• 3,5-Di-tert-butyl-4-methoxybenzaldehyde
• 4-(2,4-DICHLORO-PHENYL)-3-OXO-BUTYRIC ACID ETHYL ESTER
• 5-(2,4-DICHLORO-PHENYL)-4H-PYRAZOLE-3-CARBOXYLIC ACID
• 4-(2,4-DICHLOROPHENYL)-4-OXOBUTYRIC ACID
• ethyl 4-(2,4-dichlorophenyl)-2,4-dioxobutanoate
• (3AR,4S,9BS)-7,9-DICHLORO-3A,4,5,9B-TETRAHYDRO-3H-CYCLOPENTA[C]QUINOLINE-4-CARBOXYLIC ACID
• Benzenebutanoic acid, 2,4-dichloro-alpha-hydroxy-gamma-oxo-
• ETHYL 4-(2,4-DICHLOROPHENYL)-4-OXOBUTYRATE
• 2-AMINO-4-(2,4-DICHLORO-PHENYL)-BUTYRIC ACID