TOLUENE-4-SULFONIC ACID OXETAN-3-YL ESTER Chemical Properties

Melting point:

81.0 to 86.0 °C

Boiling point:

372℃

Density 

1.34

Flash point:

179°(354°F)

storage temp. 

Sealed in dry,Room Temperature

form 

powder to crystal

color 

White to Orange to Green

Safety Information

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

HS Code 

29309090

TOLUENE-4-SULFONIC ACID OXETAN-3-YL ESTER Usage And Synthesis

Synthesis

General procedure for the synthesis of toluene-4-sulfonic acid oxetan-3-yl ester (14) from oxetan-3-ol (13) and p-toluenesulfonyl chloride: Step 1: To a 27 mL solution of dichloromethane containing 1.00 g (13.5 mmol) of oxetan-3-ol (13) and 7.6 mL (54.0 mmol) of triethylamine, 5.15 g (27.0 mmol) of p-toluenesulfonyl chloride was added. The reaction mixture was stirred overnight at room temperature. Upon completion of the reaction, the reaction was quenched with 150 mL of saturated aqueous sodium bicarbonate and extracted with three 50 mL portions of dichloromethane. The organic phases were combined, concentrated and purified by column chromatography (silica, 0-25% ethyl acetate/hexane) to afford 1.22 g (94% yield) of toluene-4-sulfonic acid oxetan-3-yl ester (14) as a white solid. Its NMR hydrogen spectrum (CDCl3, 500 MHz) data were as follows: δ 7.78 (d, J=8.5 Hz, 2H), 7.36 (d, J=9.0 Hz, 2H), 5.29 (m, 1H), 4.69 (m, 4H), 2.46 (s, 3H).

References

[1] Patent: WO2012/138678, 2012, A1. Location in patent: Page/Page column 33
[2] Journal of Organic Chemistry, 1983, vol. 48, # 18, p. 2953 - 2956
[3] Patent: US2015/336982, 2015, A1. Location in patent: Paragraph 0290; 0291
[4] Patent: EP3342765, 2018, A1. Location in patent: Paragraph 0293
[5] Patent: US2008/9465, 2008, A1. Location in patent: Page/Page column 82

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