Ethylene Glycol → Di(2-isopropylphenyl) sulfide

HRID 2180684Notes

Reaction equation

HRID 2180684 reaction equation
C(=O)([O-])[O-].[K+].[K+].C(O)(CC)(C)C.C(O)CO.[CH:17]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1I)([CH3:19])[CH3:18].[CH:27]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[SH:36])([CH3:29])[CH3:28].CCCCCCCCCCCC>C(OCC)(=O)C>[CH:17]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[S:36][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=1[CH:27]([CH3:29])[CH3:28])([CH3:19])[CH3:18]

Participants

8

Reactant 6

HCID 174Ethylene GlycolHCID 64052-Methyl-2-butanolHCID 8182DodecaneHCID 11430Potassium CarbonateHCID 87931o-IodocumeneHCID 96003Benzenethiol, 2-(1-methylethyl)-

Product 1

HCID 11402991Di(2-isopropylphenyl) sulfideYield 91%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

Cu(I) iodide (38 mg, 0.2 mmol) and potassium carbonate (276 mg, 2.0 mmol) were charged into a screw-capped test tube with Teflon-lined septum. The tube was evacuated and backfilled with argon (3 cycles). tert-Amyl alcohol (2-methyl-2-butanol) (1.0 mL, bench grade solvent without degassing and pre-drying), ethylene glycol (111 μL, 2.0 mmol, bench grade solvent), 2-isopropyliodobenzene (246 mg, 1.0 mmol) and 2-isopropylbenzenethiol (90% purity, 202 μL, 1.2 mmol) were added by syringes at room temperature. The tube was heated to 100° C. and stirred for 24 hours. The reaction mixture was then allowed to reach room temperature. Ethyl acetate (approx. 5 mL) and dodecane (227 μL, GC standard) were added. The aliquot was analyzed GC. The reaction mixture was then filtered and concentrated. The crude product was purified by column chromatography on silica gel using hexane as eluent to afford colorless oil as the titled product (245 mg, 91% yield). Rf=0.5 (hexane). 1H NMR (CDCl3, 300 MHz) δ 7.30 (d, 2 H, J=7.2 Hz), 7.18-7.24 (m, 2 H), 7.03-7.05 (m, 4 H), 3.50 (hept, 2 H, J=6.9 Hz), 1.25 (s, 3 H), 1.23 (s, 3 H). 13C NMR (CDCl3, 75 MHz) δ 149.2, 134.2, 132.1, 127.6, 126.7, 125.9, 30.9, 23.8. IR (neat, cm−1) 3058, 2962, 2929, 2867. MS (EI) m/z (relative intensity) 270 (100), 211 (90). HRMS (EI), Cald. for C18H22S 270.1442. Found 270.1445.

Workup

  1. customThe tube was evacuated
  2. customto reach room temperature
  3. filtrationThe reaction mixture was then filtered
  4. concentrationconcentrated
  5. customThe crude product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-8bb33339740441f8b761b80142d22fe6
Source dataset
uspto-grants-2005_05
Patent number
US06888032B2

Reaction notes

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