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65874-27-3

65874-27-3 Structure

65874-27-3 Structure
IdentificationBack Directory
[Name]

4-FORMYL-BENZOIC ACID MONO TERT-BUTYL ESTER
[CAS]

65874-27-3
[Synonyms]

tert-butyl 4-forMylbenzoate
4-(tert-Butoxycarbonyl)benzaldehyde
4-Formylbenzoic Acid tert-Butyl Ester
4-FORMYL-BENZOIC ACID MONO TERT-BUTYL ESTER
4-ForMyl-benzoic acid Mono tert-butyl ester(70%)
Benzoic acid, 4-formyl-, 1,1-dimethylethyl ester
[Molecular Formula]

C12H14O3
[MDL Number]

MFCD01111994
[MOL File]

65874-27-3.mol
[Molecular Weight]

206.24
Chemical PropertiesBack Directory
[Melting point ]

52.0 to 56.0 °C
[Boiling point ]

310.7±25.0 °C(Predicted)
[density ]

1.093±0.06 g/cm3(Predicted)
[storage temp. ]

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

powder to crystal
[color ]

White to Orange to Green
Safety DataBack Directory
[Symbol(GHS) ]


GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H315-H319-H335
[Precautionary statements ]

P261-P305+P351+P338
[HS Code ]

2916399090
Spectrum DetailBack Directory
[Spectrum Detail]

4-FORMYL-BENZOIC ACID MONO TERT-BUTYL ESTER(65874-27-3)1HNMR
Hazard InformationBack Directory
[Synthesis]

Di-tert-butyl dicarbonate

24424-99-5

4-Formylbenzoic acid

619-66-9

4-FORMYL-BENZOIC ACID MONO TERT-BUTYL ESTER

65874-27-3

Example 1 Synthesis of tert-butyl 4-formylbenzoate: To a 250 mL round bottom flask were sequentially added tert-butyl para-formylbenzoate (5.0 g, 33 mmol), di-tert-butyl dicarbonate (14.54 g, 66.6 mmol), 4-dimethylaminopyridine (0.814 g, 6.66 mmol) and tetrahydrofuran (100 mL). The reaction mixture was stirred at room temperature for 16 hours. After completion of the reaction, the solvent was removed by distillation under reduced pressure to give the crude product. Ethyl acetate (150 mL) was added to the residue and washed with saturated sodium bicarbonate solution (25 mL) and water (25 mL). After partitioning, the aqueous phase was back-extracted with ethyl acetate (2 x 100 mL). The organic phases were combined, washed with saturated saline (50 mL), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. Finally, it was purified by fast column chromatography (eluent: petroleum ether to 10% ethyl acetate-petroleum ether gradient elution) to give tert-butyl 4-formylbenzoate (1.90 g, 28% yield) as a white solid. The product was characterized by 1H NMR (CDCl3, 400 MHz): δ 10.10 (s, 1H), 8.14 (d, J = 8.3 Hz, 2H), 7.93 (d, J = 8.5 Hz, 2H), 1.61 (s, 9H).

[References]

[1] Journal of the American Chemical Society,
[2] Journal of the American Chemical Society, 2009, vol. 131, p. 7488 - 7489
[3] Patent: US2003/176495, 2003, A1
[4] Patent: US2011/212969, 2011, A1. Location in patent: Page/Page column 109
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