tert-butyl 4-hydroxybenzoate Chemical Properties

Melting point:

130-132 °C(Solv: ethyl ether (60-29-7); ligroine (8032-32-4))

Boiling point:

295.6±13.0 °C(Predicted)

Density 

1.107±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

form 

solid

pka

8.25±0.15(Predicted)

color 

White

Safety Information

HS Code 

2918290090

tert-butyl 4-hydroxybenzoate Usage And Synthesis

Uses

4-Hydroxybenzoate tert-butyl ester is used in organic synthesis, biochemical research, etc.

Synthesis

Using p-hydroxybenzoic acid (1.50 g, 10.86 mmol) and tert-butanol (13.34 g, 18 mmol) as raw materials, DCC (2.5 g, 12.00 mmol) was dissolved in DCM (40 mL) catalyzed by DBU (0.19 mL, 1.20 mmol), and the reaction mixture was stirred vigorously for 18 hours at room temperature. After completion of the reaction, the solvent was evaporated to dryness and the residue was dissolved in DCM (50 mL) and filtered to remove insoluble material. The filtrate was washed sequentially with saturated NaHCO3 solution (50 mL), K2CO3 solution (2 x 50 mL) and saturated NaCl solution (50 mL). The organic phase was dried with MgSO4, filtered and the solvent was evaporated to give the crude product. The crude product was purified by column chromatography (EtOAc:hexane gradient elution) to afford tert-butyl 4-hydroxybenzoate (SO2-059) (31) as a white crystalline solid (1.1 g, 55% yield).1H NMR (400 MHz, CDCl3) δ 7.89 (d, J = 8.8 Hz, 1H), 6.84 (d, J = 8.9 Hz, 1H) 5.29 (s, 1H), 1.57 (s, 9H).

References

[1] Journal of Materials Chemistry, 2007, vol. 17, # 48, p. 5097 - 5110
[2] Synthesis, 2003, # 16, p. 2479 - 2482
[3] European Journal of Medicinal Chemistry, 2015, vol. 101, p. 716 - 735
[4] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 14, p. 3645 - 3649
[5] Journal of Medicinal Chemistry, 2013, vol. 56, # 10, p. 3783 - 3805

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