P-Cresol → 1-(3-Chloropropoxy)-4-methylbenzene

HRID 1739405Notes

Reaction equation

HRID 1739405 reaction equation
[CH:1]1[C:6]([OH:7])=[CH:5][CH:4]=[C:3]([CH3:8])[CH:2]=1.Br[CH2:10][CH2:11][CH2:12][Cl:13].[OH-].[Na+]>O>[C:3]1([CH3:8])[CH:4]=[CH:5][C:6]([O:7][CH2:10][CH2:11][CH2:12][Cl:13])=[CH:1][CH:2]=1

Participants

5

Reactant 3

HCID 2879P-CresolHCID 80061-Bromo-3-chloropropaneHCID 14798Sodium Hydroxide2×

Product 1

HCID 126856111-(3-Chloropropoxy)-4-methylbenzeneYield 76.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3.0 g of p-cresol and 4.0 g of 3-bromo-1-chloro propane were placed into 20 ml of water and were subjected to reflux for 1 hour under heating, and whereto 20 ml of the aqueous solution of sodium hydroxide containing 1.2 g of sodium hydroxide were fed dropwise. After subjecting the resultant solution prepared as described hereinabove to reflux for another 2 hours, the solution reacted was poured into ice-water and extracted with ethyl acetate. The ethyl acetate layer resulted was washed with dilute aqueous alkaline solution and saturated saline solution in series, and the organic layer resulted was then dried with anhydrous magnesium sulfate, and the solvent used was removed by distillation under reduce pressure, thereby affording 3.6 g of 3-(4-tolyloxy)-1-chloro propane.

Workup

  1. temperatureto reflux for 1 hour
  2. temperatureunder heating
  3. customprepared
  4. temperatureto reflux for another 2 hours
  5. customthe solution reacted
  6. extractionextracted with ethyl acetate
  7. customThe ethyl acetate layer resulted
  8. washwas washed with dilute aqueous alkaline solution and saturated saline solution in series
  9. customthe organic layer resulted
  10. dry with materialwas then dried with anhydrous magnesium sulfate
  11. customthe solvent used was removed by distillation

Sources & evidence

ORD record
ord-7343551695d44146a3191526e3b5cec1
Source dataset
uspto-grants-1999_10
Patent number
US05965743

Reaction notes

Loading…