2-Thiocresol → (2,2-Diethoxyethyl)(o-tolyl)sulfane

HRID 1372274Notes

Reaction equation

HRID 1372274 reaction equation
[Na].[CH3:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[SH:9].[CH2:10]([O:12][CH:13]([O:16][CH2:17][CH3:18])[CH2:14]Br)[CH3:11]>C(O)C>[CH2:10]([O:12][CH:13]([O:16][CH2:17][CH3:18])[CH2:14][S:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[CH3:2])[CH3:11]

Participants

5

Reactant 3

HCID 87122-ThiocresolHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 5360545Sodium

Product 1

HCID 10610097(2,2-Diethoxyethyl)(o-tolyl)sulfaneYield 89%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In ethanol (50 mL) was dissolved sodium metal (1.6 g, 66 mmol) at 23° C. 2-Methylbenzenethiol (8.1 mL, 68 mmol) was slowly added to this solution, followed by bromoacetaldehyde diethylacetal (9.50 mL, 63 mmol). The reaction mixture was stirred at reflux for 18 h. The solvent was then evaporated in vacuo and the residue was washed with H2O (100 mL) and extracted with ether (100 mL). The organic solution was dried (MgSO4), concentrated in vacuo and purified by distillation to afford the title compound (13.48 g, 82% yield): 1H NMR (400 MHz, CDCl3) δ ppm: 7.33 (1H, d, J=7.9 Hz), 7.16–7.08 (3H, m), 4.65 (1H, t, J=5.6 Hz), 3.66 (2H, q, J=7.0 Hz), 3.55 (2H, q, J=7.0 Hz), 3.09 (2H, d, J=5.6 Hz), 2.38 (3H, s), 1.20 (6H, t, J=7.0 Hz). LCMS (M+H)+ m/z 241 (t=2.65 min.).

Workup

  1. temperatureat reflux for 18 h
  2. customThe solvent was then evaporated in vacuo
  3. washthe residue was washed with H2O (100 mL)
  4. extractionextracted with ether (100 mL)
  5. dry with materialThe organic solution was dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. distillationpurified by distillation

Sources & evidence

ORD record
ord-c92a487990b145c99f57d0376a4c1432
Source dataset
uspto-grants-2007_01
Patent number
US07157447B2

Reaction notes

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