Water → P-Cresol

HRID 2296528Notes

Reaction equation

HRID 2296528 reaction equation
[Cl:1]Cl.[CH:3]1[C:8]([OH:9])=[CH:7][CH:6]=[C:5]([CH3:10])[CH:4]=1.O>C(Cl)(Cl)(Cl)Cl>[CH:7]1[C:8]([OH:9])=[CH:3][CH:4]=[C:5]([CH3:10])[CH:6]=1.[Cl:1][C:7]1[C:8]([OH:9])=[CH:3][CH:4]=[C:5]([CH3:10])[CH:6]=1

Participants

6

Reactant 3

HCID 962WaterHCID 2879P-CresolHCID 24526Chlorine

Product 2

HCID 2879P-CresolYield 96.6%HCID 148512-Chloro-4-methylphenolYield 3.3%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Four grams of chlorine was bubbled through a stirred solution of 10.8 g of p-cresol (10 mmoles) in 100 ml of carbon tetrachloride for about 30 minutes. A five-gram sample, removed and analyzed and showed 46.9% p-cresol and 53.1% 2-chloro-p-cresol. Then 0.1 ml of ethanol and 10.00 g powdered anhydrous calcium bromide were added to the chlorinated p-cresol mixture. The mixture was stirred in the absence of atmospheric moisture for about 16 hours. A washed-and-dried solid was obtained weighing 10.40 g. A sample of the solid was hydrolyzed by water and extracted five times with carbon tetrachloride. GC analysis of the combined extract gave 96.6% p-cresol and 3.3% 2-chloro-p-cresol, showing substantially complete separation of p-cresol from its chlorinated derivative by complexation with calcium bromide.

Workup

  1. customA five-gram sample, removed
  2. additionwere added to the chlorinated p-cresol mixture
  3. washA washed-
  4. custom-dried solid
  5. customwas obtained
  6. extractionextracted five times with carbon tetrachloride
  7. extractionGC analysis of the combined extract

Sources & evidence

ORD record
ord-e51e18429156429188ad94c627a69dcb
Source dataset
uspto-grants-1984_01
Patent number
US04429168

Reaction notes

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