Sodium Hydroxide → 3-(4-Methoxyphenyl)propane-1-thiol

HRID 363445Notes

Reaction equation

HRID 363445 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11]Br)=[CH:5][CH:4]=1.NC(N)=[S:15].[OH-].[Na+]>C(O)C.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][SH:15])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 2723790ThioureaHCID 127769961-(3-Bromopropyl)-4-methoxybenzene

Product 1

HCID 131223923-(4-Methoxyphenyl)propane-1-thiol

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 3-(p-methoxyphenyl)-1-propylbromide (14 g; 61 mmol) and thiourea (5.1 g; 67 mmol) in ethanol (150 mL) was refluxed for 48 hours. Evaporation of the solvent provided a clear glassy compound, which was dissolved in 50 mL of water and treated with 100 mL of 40% aqueous sodium hydroxide. After stirring the resulting mixture for two hours, the product was extracted into ether (3×), and the combined organic extracts were washed with sodium bicarbonate and brine, dried, and concentrated. Chromatographic purification of the crude thiol on a silica gel column eluting with 2% either in hexane delivered 10.2 g of 3-(p-methoxyphenyl)-1-propylmercaptan as a clear liquid 1H NMR (300 MHz, CDCl3):δ 1.34 (t, 1H); 1.88-1.92 (m,2H); 2.49-2.53 (m,2H); 2.64-2.69 (m, 2H); 3.77 (s, 3H); 6.80-6.84 (m,2H); 7.06-7.24 (m,2H).

Workup

  1. temperaturewas refluxed for 48 hours
  2. customEvaporation of the solvent
  3. customprovided a clear glassy compound, which
  4. extractionthe product was extracted into ether (3×)
  5. washthe combined organic extracts were washed with sodium bicarbonate and brine
  6. customdried
  7. concentrationconcentrated
  8. customChromatographic purification of the crude thiol on a silica gel column
  9. washeluting with 2% either in hexane

Sources & evidence

ORD record
ord-915671ab5d7948359cb33e5b485ddbe8
Source dataset
uspto-grants-1999_02
Patent number
US05874449

Reaction notes

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