6-Mercaptohexan-1-ol synthesis

7synthesis methods

Product Name:6-Mercaptohexan-1-ol
CAS Number:1633-78-9
Molecular formula:C6H14OS
Molecular Weight:134.24

4286-55-9

1633-78-9

The general procedure for the synthesis of 6-mercaptohexan-1-ol from 6-bromohexanol was as follows: 6-bromohexanol (1 g, 5.60 mmol) was mixed with thiourea (0.64 g, 8.40 mmol) and NaOH (0.1 M) in 1,4-dioxane (4 mL), and the reaction was carried out at reflux for 4 hours. After completion of the reaction, the reaction mixture was cooled and the solvent was removed under vacuum. Subsequently, the pH of the reaction mixture was adjusted to 4 by addition of dilute hydrochloric acid. hydrochloric acid and thiol derivatives in the reaction mixture were extracted with dichloromethane. The organic layer was dried with anhydrous sodium sulfate and then concentrated to give 6-mercaptohexan-1-ol as a yellow oil. Yield: 0.563 g (75%). The structure of the product was determined by 1H NMR (500 MHz, DMSO-d6, TMS): δ 3.65 (s, 1H), 3.5 (t, 2H, J = 2.4Hz), 2.56 (t, 2H, J = 2.3Hz), 1.52-1.57 (m, 4H), 1.5 (s, 1H), 1.41-1.44 (m, 4H); 13C NMR ( 125 MHz, DMSO): δ 62.8,34.5,32.3,28.2,24.9,24.6; ESI-MS: m/z calculated values. For C6H14OS: 134.08, measured value: 135.11 (M++1) for confirmation.

4286-55-9
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1633-78-9
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Yield:1633-78-9 75%

Reaction Conditions:

with thiourea;sodium hydroxide in 1,4-dioxane at 80;

Steps:

2.2 Synthesis of 6-mercapto-hexan-1-ol
6-Bromohexanol (1 g, 5.60 mmol) was allowed to reflux withthiourea (0.64 g, 8.40 mmol) and NaOH (0.1 M) in 1,4-dioxane (4 mL) for 4 h. The reaction mixture was cooledand the solvent was removed under vacuum. The pH of thereaction mixture was adjusted to 4 by adding dilute. HCl andthe thiol derivative was extracted using dichloromethane. Theorganic layerwas dried overNa2SO4 and concentrated to give6-mercaptohexanol as an yellow oil.Yield: 0.563 g (75%); 1H NMR (500 MHz, DMSO-d6,TMS): δ 3.65 (s, 1H), 3.5 (t, 2H, J = 2.4Hz), 2.56 (t, 2H,J = 2.3Hz), 1.52-1.57 (m, 4H), 1.5 (s, 1H), 1.41-1.44 (m,4H); 13C NMR (125 MHz, DMSO): δ 62.8, 34.5, 32.3, 28.2,24.9, 24.6; ESI-MS:m/z Calcd. forC6H14OS: 134.08, Found:135.11 (M+ + 1).

References:

Paul, Albish K;Jayaram, Dhanya T;Babu, P S Saneesh;Adarsh, Nagappanpillai;Thurakkal, Shameel;Nair, Asha S;Ramaiah, Danaboyina [Journal of Chemical Sciences,2018,vol. 130,# 10,art. no. 133]

FullText

2009-83-8 Synthesis