4-Tritylsulfanylbutanoic acid synthesis
- Product Name:4-Tritylsulfanylbutanoic acid
- CAS Number:377733-71-6
- Molecular formula:C23H22O2S
- Molecular Weight:362.48
76-83-5
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Yield:377733-71-6 90%
Reaction Conditions:
in N,N-dimethyl-formamide at 20; for 120 h;
Steps:
3.1.1. 4-(Tritylthio)butanoic acid (5) [49]
4-Bromobutyric acid 3 (16.48 g, 98 mmol) was refluxed for 3 h with thiourea (8.5 g, 107 mmol) in 30 mL ethanol. Then 50 mL of aqueous NaOH (4 M, 200 mmol) was added and refluxing was continued for another 2 h. The solution was concentrated in vacuo,acidified with aqueous HCl (6 M), and extracted with ether, the extract dried over anhydrous sodium sulfate (Na2SO4), evaporated,and the residue distilled in vacuo to give compound 4 (10.45 g, 87.1 mmol, 87%) as a light pink oil. Then, mixture of compound 4 (3 g, 25 mmol) and trityl chloride (10 g, 38 mmol) were stirred in 40 mL DMF for 5 days at room temperature. A 10% sodium acetate solution (350 mL) was then added, and the precipitate was filtered and washed with water. The product was distilled in vacuo to give compound 5 (8.1 g, 22.5 mmol, 90%) as white powder. 1H NMR (400 MHz, CDCl3) d7.43e7.37 (m, 6H, ArH), 7.29e7.23 (m, 6H, ArH),7.22e7.15 (m, 3H, ArH), 2.38 (t, J 7.4 Hz, 2H, -CH2COO-), 2.30 (t,J 7.2 Hz, 2H, -CH2S-), 1.76e1.73 (m, 2H, -CH2-).
References:
Yang, Qinglai;He, Changyu;Zhang, Zhen;Tan, Lianjiang;Liu, Bingya;Zhu, Zhenggang;Shao, Zhifeng;Gong, Bing;Shen, Yu-Mei [Polymer,2016,vol. 90,p. 351 - 362]
76-84-6
421 suppliers
$6.00/25g
13095-73-3
85 suppliers
$81.59/100mg
377733-71-6
5 suppliers
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