Ethylene Oxide → 4-Ethylthiophenethyl alcohol

HRID 981137Notes

Reaction equation

HRID 981137 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][CH3:10])=[CH:4][CH:3]=1.[Mg].[CH2:12]1[O:14][CH2:13]1.[Cl-].[NH4+]>C1COCC1>[CH2:9]([S:8][C:5]1[CH:6]=[CH:7][C:2]([CH2:12][CH2:13][OH:14])=[CH:3][CH:4]=1)[CH3:10]

Participants

6

Reactant 4

HCID 6354Ethylene OxideHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 70066501-Bromo-4-(ethylthio)benzene

Product 1

HCID 27589134-Ethylthiophenethyl alcoholYield 16%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1-Bromo-4-(ethylthio)benzene (16.0 g) in THF (80 ml) was added dropwise to magnesium (1.82 g) to maintain gentle reflux. The resulting cloudy solution was cooled to 0° and ethylene oxide (6.6 g) in THF (10 ml) was added dropwise. The mixture was stirred at room temperature for 30 min and at reflux for 1 h. Saturated aqueous ammonium chloride (200 ml) was added and the mixture was extracted with ER (2×200 ml). The dried extracted was evaporated and the residue was purified by [C] eluting with cyclohexane-ER (7.3) to give the title alcohol (2.15 g). T.l.c. (cyclohexane-ER 1:1) Rf 0.4.

Workup

  1. temperatureto maintain gentle reflux
  2. temperatureThe resulting cloudy solution was cooled to 0°
  3. temperatureat reflux for 1 h
  4. extractionthe mixture was extracted with ER (2×200 ml)
  5. extractionThe dried extracted
  6. customwas evaporated
  7. customthe residue was purified by [C]
  8. washeluting with cyclohexane-ER (7.3)

Sources & evidence

ORD record
ord-6ff19ac566d24cf8b2aa94f5655e447e
Source dataset
uspto-grants-1991_02
Patent number
US04990505

Reaction notes

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