Water → HCID 15662557, compound

HRID 1073424Notes

Reaction equation

HRID 1073424 reaction equation
[CH3:1][CH:2]([S:5][C:6]1[CH:11]=[CH:10][C:9]([SH:12])=[CH:8][CH:7]=1)[CH2:3][CH3:4].C(=O)([O-])[O-].[K+].[K+].[C:19]([O:22][CH2:23][CH2:24]Br)(=[O:21])[CH3:20].O>CN(C=O)C>[C:19]([O:22][CH2:23][CH2:24][S:12][C:9]1[CH:8]=[CH:7][C:6]([S:5][CH:2]([CH3:1])[CH2:3][CH3:4])=[CH:11][CH:10]=1)(=[O:21])[CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 135641-Acetoxy-2-bromoethaneHCID 15662554HCID 15662554, compound

Product 1

HCID 15662557HCID 15662557, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 4-(1-methylpropylthio)benzenethiol (53.7 g, 271.0 mmol) and potassium carbonate (49.4 g, 358.0 mmol) in DMF under N2 and with stirring is added dropwise 2-bromoethyl acetate (34.0 ml, 298.0 mmol). The mixture is stirred at RT overnight, after which water is added and the mixture is extracted with ether. The combined organic layers are washed with water and brine, dried, the solvent removed and the residue purified by distillation to give 2-[4-(1-methylpropylthio)phenylthio]ethyl acetate. To the acetate (60.9 g, 214.0 mmol) in 200 ml of ethanol is added 50% sodium hydroxide (20 ml). The reaction mixture is stirred at RT for 7 hours and is then neutralized by addition of 10% sulfuric acid and extracted with ether. The organic layer is washed with water and brine, dried and the solvent removed to give 2-[4-(1methylpropylthio)phenylthio]ethanol.

Workup

  1. stirringThe mixture is stirred at RT overnight
  2. extractionthe mixture is extracted with ether
  3. washThe combined organic layers are washed with water and brine
  4. customdried
  5. customthe solvent removed
  6. distillationthe residue purified by distillation

Sources & evidence

ORD record
ord-87c2207da835473fa33b191dbc5901d2
Source dataset
uspto-grants-1990_11
Patent number
US04968829

Reaction notes

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