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

HRID 1709867Notes

Reaction equation

HRID 1709867 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].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:13][CH2:12][CH2:11][CH2:10][O:7][C:6]1[CH:5]=[CH:4][C:3]([CH3:8])=[CH:2][CH:1]=1

Participants

5

Reactant 3

HCID 2879P-CresolHCID 80061-Bromo-3-chloropropaneHCID 11430Potassium Carbonate

Product 1

HCID 126856111-(3-Chloropropoxy)-4-methylbenzeneYield 102%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 27 g (0.25 mole) of p-cresol, 78.7 g (0.5 mole) of 1-bromo-3-chloropropane and 103.7 g (0.75 mole) of anhydrous potassium carbonate in 1 liter of acetone was heated at reflux for 24 hr. The reaction mixture was cooled, filtered and concentrated in vacuo at 90° C. to give 47.1 g of an oil residue. The oil was subjected to vacuum distillation to give 39.3 g (85%) of clear oil, bp 85°-90° C. at 0.1 mm Hg.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 24 hr
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo at 90° C.

Sources & evidence

ORD record
ord-f8c3d62457174ebf875217f7b5ec430e
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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