Ethylene Glycol → HCID 12026851, compound

HRID 2180672Notes

Reaction equation

HRID 2180672 reaction equation
I[C:2]1[CH:3]=[C:4]([CH3:9])[CH:5]=[C:6]([CH3:8])[CH:7]=1.[SH:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1.C([O-])([O-])=O.[K+].[K+].C(O)CO>[Cu]I.CC(O)C>[CH3:8][C:6]1[CH:7]=[C:2]([S:10][C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)[CH:3]=[C:4]([CH3:9])[CH:5]=1

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 11430Potassium CarbonateHCID 1409241-Iodo-3,5-dimethylbenzeneHCID 2401474-Mercaptophenol

Product 1

HCID 12026851HCID 12026851, compoundYield 90%

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), 4-mercaptophenol (126 mg, 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 4-(3,5-dimethylphenyl)sulfanylphenol (207 mg, 90% yield) as colorless liquid. Workup procedure: ethyl acetate (approx. 5 mL) and dodecane (227 μL, GC standard) were added to the reaction mixture after the reaction was completed. The organic layer was neutralized by dilute HCl to pH 8. The aqueous layer was extracted by ethyl acetate (4×10 mL). The combined organic layers were concentrated and purified by column chromatography on silica gel using hexane/ethyl acetate=10/1 as the eluent to afford the titled product. Rf=0.3 (hexane/ethyl acetate=10/1). 1H NMR (CDCl3, 300 MHz) δ 7.33 (dt, 2 H, J=1.8 Hz, 8.4 Hz), 6.77-6.81 (m, 5 H), 4.83 (s, 1 H), 2.22 (s, 6 H). 13C NMR (CDCl3, 75 MHz) δ 155.6, 138.8, 137.7, 135.4, 128.1, 126.4, 125.3, 116.6, 21.6. IR (neat, cm−1) 3371 (broad), 3031, 2917, 2860. MS (EI) m/z (relative intensity) 230 (100), 215 (20). Anal Cald for C14H14OS, Cald. C, 73.01; H, 6.13. Found C, 73.21; H, 6.11.

Sources & evidence

ORD record
ord-6e042ba51739421291949288278d8828
Source dataset
uspto-grants-2005_05
Patent number
US06888032B2

Reaction notes

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