Ethylene Glycol → HCID 22492579, compound

HRID 2253524Notes

Reaction equation

HRID 2253524 reaction equation
I[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[CH3:10][O:11][C:12]1[CH:13]=[C:14]([SH:18])[CH:15]=[CH:16][CH:17]=1.C([O-])([O-])=O.[K+].[K+].C(O)CO>[Cu]I.CC(O)C>[CH3:10][O:11][C:12]1[CH:13]=[C:14]([S:18][C:2]2[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=2)[CH:5]=[O:6])[CH:15]=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 11430Potassium CarbonateHCID 849893-MethoxybenzenethiolHCID 2526103-Iodobenzaldehyde

Product 1

HCID 22492579HCID 22492579, compoundYield 85%

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. 3-Iodobenzaldehyde (232 mg, 1.0 mmol), 3-methoxythiophenol (124 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 3-(3-methoxyphenyl)sulfanylbenzaldehyde (205 mg, 85% yield) as colorless liquid. Column chromatographic solvent (hexane/ethyl acetate=15/1). Rf=0.4 hexane/ethyl acetate=10/1). 1H NMR (CDCl3, 300 MHz) δ 9.91 (s, 1 H), 7.76-7.77 (m, 1 H), 7.71 (dt, 1 H, J=1.2 Hz, 7.2 Hz), 7.45-7.53 (m, 1 H), 7.42 (t, 1 H, J=7.5 Hz), 7.25 (t, 1 H, J=7.5 Hz), 6.91-6.98 (m, 2 H), 6.84 (ddd, 1 H, J=1.2 Hz, 2.4 Hz, 8.1 Hz), 3.77 (s, 3 H). 13C NMR (CDCl3, 75 MHz) δ 191.7, 160.3,138.4,137.3, 135.8,135.0,131.1, 130.5,129.9,127.9, 124.6,117.6,114.0,55.7. IR (neat, cm−1) 3060, 3006, 2960, 2937, 2834, 2726, 1698. MS (EI) m/z (relative intensity) 244 (100), 227 (30), 211 (40). Anal. Cald. for C14H12O2S, Cald. C: 68.83, H: 4.95; Found C: 69.04, H: 4.94.

Sources & evidence

ORD record
ord-30db2b0e49334d839b504917fdbcd9d9
Source dataset
uspto-grants-2008_01
Patent number
US07323608B2

Reaction notes

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