4-Chlorophenol → 1-(4-chlorophenoxy)propan-2-ol

HRID 1704126Notes

Reaction equation

HRID 1704126 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[H-].[Na+].[I-].[K+].Cl[CH2:14][CH:15]([OH:17])[CH3:16]>O1CCCC1.C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:14][CH:15]([OH:17])[CH3:16])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 46844-ChlorophenolHCID 4875Potassium IodideHCID 24758Sodium hydrideHCID 313701-Chloro-2-propanol

Product 1

HCID 2203171-(4-chlorophenoxy)propan-2-ol

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
80 °C

Procedure

To a solution of 3.87 g of p-chlorophenol in 30 ml of tetrahydrofuran is added 1.2 g of sodium hydride (60% dispersion in oil). After one hour, 4.98 g of potassium iodide and 2.54 ml of 1-chloro-2-propanol in 10 ml of tetrahydrofuran is added. The mixture is heated at 80° C. for 18 hours. The mixture is chilled, poured into 300 ml of ice-water containing 3 ml of acetic acid. The mixture is extracted with dichloromethane and the extract washed with saturated sodium bicarbonate and sodium chloride solution. Drying (MgSO4) and removal of the solvent under reduced pressure gives 5.1 g of product as an oil.

Workup

  1. temperatureThe mixture is chilled
  2. extractionThe mixture is extracted with dichloromethane
  3. washthe extract washed with saturated sodium bicarbonate and sodium chloride solution
  4. customDrying
  5. custom(MgSO4) and removal of the solvent under reduced pressure

Sources & evidence

ORD record
ord-cf48548e303c44b4ad22e08d3fdf28a3
Source dataset
uspto-grants-1978_11
Patent number
US04125732

Reaction notes

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