Water → HCID 14852817, compound

HRID 2248168Notes

Reaction equation

HRID 2248168 reaction equation
[C:1]1(=O)[O:5][CH2:4][CH2:3][O:2]1.C(=O)([O-])[O-].[K+].[K+].[CH3:13][CH:14]([S:17][C:18]1[CH:23]=[CH:22]C(O)=[CH:20][CH:19]=1)[CH2:15][CH3:16].O>CN(C=O)C>[CH3:13][CH:14]([S:17][C:18]1[CH:23]=[CH:22][C:1]([O:2][CH2:3][CH2:4][OH:5])=[CH:20][CH:19]=1)[CH2:15][CH3:16]

Participants

6

Reactant 4

HCID 962WaterHCID 7303Ethylene carbonateHCID 11430Potassium CarbonateHCID 14650104HCID 14650104, compound

Product 1

HCID 14852817HCID 14852817, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of ethylene carbonate (41.08 g, 460.0 mmol) and potassium carbonate (63.57 g, 460.0 mmol) in 100 ml of DMF is heated to 110° and 4-(1-methylpropylthio)phenol (40.19 g, 230.0 mmol) in 100 ml DMF is slowly added dropwise with stirring. The mixture is stirred at 100° for 8 hours. Water is added to the cooled reaction mixture and the aqueous phase is extracted with ether. The combined organic layers are washed with 5% NaOH, with water and with brine, dried and the solvent removed to give 2-[4-(1-methylpropylthio)phenoxy]ethanol.

Workup

  1. temperatureis heated to 110°
  2. stirringThe mixture is stirred at 100° for 8 hours
  3. extractionthe aqueous phase is extracted with ether
  4. washThe combined organic layers are washed with 5% NaOH, with water and with brine
  5. customdried
  6. customthe solvent removed

Sources & evidence

ORD record
ord-38994345d8be4453b2d1ac414993e3e5
Source dataset
uspto-grants-1991_08
Patent number
US05037991

Reaction notes

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