2,4-Dichlorophenol → (2,4-Dichlorophenoxy)propanol

HRID 1939150Notes

Reaction equation

HRID 1939150 reaction equation
Br[CH2:2][CH2:3][CH2:4][OH:5].[Cl:6][C:7]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:8]=1[OH:14].N12CCCN=C1CCCCC2>C(O)(C)C.C(Cl)Cl>[Cl:6][C:7]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:8]=1[O:14][CH2:2][CH2:3][CH2:4][OH:5]

Participants

6

Reactant 3

HCID 84492,4-DichlorophenolHCID 123083-Bromo-1-propanolHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 235019(2,4-Dichlorophenoxy)propanolYield 105.9%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-bromopropanol (53.86 g, 0.368 mol) in isopropanol is added dropwise to a mixture of 2,4-dichlorophenol (50 g, 0.307 mol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (70.05 g, 0.406 mol) in isopropanol at reflux. The reaction mixture is heated at reflux for 3 hours and concentrated in vacuo to obtain a residue. The residue is dissolved in methylene chloride and the organic solution is washed sequentially with 0.5N sodium hydroxide solution, 1M hydrochloric acid and brine, dried over MgSO4 and concentrated in vacuo to obtain an oil which solidifies to give the title product as a white solid (71.9 g, mp 53°-55° C.).

Workup

  1. temperatureat reflux
  2. temperatureThe reaction mixture is heated
  3. temperatureat reflux for 3 hours
  4. concentrationconcentrated in vacuo
  5. customto obtain a residue
  6. washthe organic solution is washed sequentially with 0.5N sodium hydroxide solution, 1M hydrochloric acid and brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customto obtain an oil which

Sources & evidence

ORD record
ord-de05edcca3cf4b73852ddb71d1874a57
Source dataset
uspto-grants-1997_12
Patent number
US05696050

Reaction notes

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