Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethylene Glycol | HCID 174 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Cyclohexanethiol | HCID 15290 | — |
| 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 22492575 | HCID 22492575 | 71% |
Reaction Steps
The general procedure in example 39 was followed. 5-Iodo-m-Xylene (144 μL, 1.0 mmol), cyclohexylmercaptan (122 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 cyclohexyl 3,5-dimethylphenyl sulfide (156 mg, 71% yield) as colorless oil. Column chromatographic solvent (hexane). Rf=0.4 (hexane). 1H NMR (CDCl3, 300 MHz) δ 6.99 (s, 2 H), 6.82 (s, 1 H), 3.02-3.10 (m, 1 H), 2.28 (s, 6 H), 1.96-2.00 (m, 2 H), 1.74-1.77 (m, 2 H), 1.56-1.63 (m, 1 H), 1.21-1.42 (m, 4 H). 13C NMR (CDCl3, 75 MHz) δ 138.4, 134.7, 129.7, 128.7, 46.8, 33.8, 26.5, 26.2, 21.6. IR (neat, cm−1) 3088, 3060, 3012, 2962, 2867. MS (EI) m/z (relative intensity) 220 (40), 138 (100), 105 (30). Anal Cald for C14H20S, Cald. C: 76.30, H: 9.15; Found C: 76.30, H: 9.17.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07323608B2 |
|---|
| Source dataset | uspto-grants-2008_01 |
|---|
| ORD ID | ord-46e900f4e09f43d3982ad19b0307ba7c |
|---|
| Source note | uspto-grants-2008_01 |
|---|
