Ethylene Glycol → HCID 11206357, compound

HRID 2253536Notes

Reaction equation

HRID 2253536 reaction equation
I[C:2]1[CH:3]=[C:4]([CH3:9])[CH:5]=[C:6]([CH3:8])[CH:7]=1.[CH2:10]([SH:14])[CH2:11][CH2:12][CH3:13].C([O-])([O-])=O.[K+].[K+].C(O)CO>[Cu]I.CC(O)C>[CH3:8][C:6]1[CH:7]=[C:2]([S:14][CH2:10][CH2:11][CH2:12][CH3:13])[CH:3]=[C:4]([CH3:9])[CH:5]=1

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 8012ButanethiolHCID 11430Potassium CarbonateHCID 1409241-Iodo-3,5-dimethylbenzene

Product 1

HCID 11206357HCID 11206357, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 3776IsopropanolSolvent

Procedure

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.

Sources & evidence

ORD record
ord-2319b2d703b34c85a48a5b6fccfd731e
Source dataset
uspto-grants-2008_01
Patent number
US07323608B2

Reaction notes

Loading…