Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethylene Glycol | HCID 174 | — |
| Reactant | Butanethiol | HCID 8012 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 1-Iodo-3,5-dimethylbenzene | HCID 140924 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Isopropanol | HCID 3776 | — |
| Product | HCID 11206357 | HCID 11206357 | 95% |
Reaction Steps
The general procedure in example 39 was followed. 5-Iodo-m-xylene (144 μL, 1.0 mmol), 1-butanethiol (107 μL, 1.0 mmol), CuI (10 mg, 0.05 mmol), K2CO3 (276 mg, 2.0 mmol), ethylene glycol (111 μL, 2.0 mmol) and 2-propanol (1.0 mL) were used to obtain the n-butyl 3,5-dimethylphenyl sulfide (184 mg, 95% yield) as colorless oil. Column chromatographic solvent (hexane). Rf=0.5 (hexane). 1H NMR (CDCl3, 300 MHz) δ 6.92 (s, 2 H), 6.77 (s, 1 H), 2.89 (t, 2 H, J=7.2 Hz), 2.27 (s, 6 H), 1.41-1.65 (m, 4 H), 0.92 (t, 3 H, J=7.5 Hz). 13C NMR (CDCl3, 75 MHz) δ 138.5, 136.7, 127.7, 126.6, 33.5, 31.6, 22.4, 21.7, 14.1. IR (neat, cm−1) 3083, 3050, 3011, 2965, 2867. MS (EI) m/z (relative intensity) 194 (70), 138 (100). Anal Cald for C12H18S, Cald. C, 74.16; H, 9.34. Found C, 73.89; H, 9.32.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06888032B2 |
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| Source dataset | uspto-grants-2005_05 |
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| ORD ID | ord-0b304914ae4f488fa939b56ac259ff99 |
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| Source note | uspto-grants-2005_05 |
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