4-Chlorophenol → Benzene, 1-chloro-4-ethoxy-

HRID 434855Notes

Reaction equation

HRID 434855 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[CH2:9](I)[CH3:10].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:9]([O:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[CH3:10]

Participants

5

Reactant 3

HCID 46844-ChlorophenolHCID 6340IodoethaneHCID 11430Potassium Carbonate

Product 1

HCID 69326Benzene, 1-chloro-4-ethoxy-

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

p-Chlorophenol (10 g., 0.077 mole), ethyl iodide (13.1 g., 0.084 mole) and anhydrous potassium carbonate (10.6 g., 0.077 mole) were combined in 130 ml. of acetone and the stirred mixture heated to reflux for 16 hours. The reaction mixture was filtered and the filtrate evaporated to dryness. The residue was taken up in 300 ml. of chloroform, washed in sequence with two 120 ml. portions of 1 N sodium hydroxide, 50 ml. of brine and 50 ml. of water, dried over anhydrous magnesium sulfate, filtered and evaporated to yield 4-ethoxyphenyl chloride as an oil [10.5 g.; pnmr/CDCl3 /delta 1.4 (t, 3H), 4.0 (q, 2H), 6.6-7.3 (m, 4H)].

Workup

  1. temperatureto reflux for 16 hours
  2. filtrationThe reaction mixture was filtered
  3. customthe filtrate evaporated to dryness
  4. washof chloroform, washed in sequence with two 120 ml
  5. dry with materialof water, dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-f5c487857bd942469068490df0b247ca
Source dataset
uspto-grants-1983_08
Patent number
US04399296

Reaction notes

Loading…