1,3-Dichloropropane → HCID 21389473, compound

HRID 459187Notes

Reaction equation

HRID 459187 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11](O)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:22][CH2:23][CH2:24]Cl>CCC(C)=O.CO>[O:1]([C:8]1[CH:13]=[CH:12][C:11]([CH2:22][CH2:23][CH3:24])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 88811,3-DichloropropaneHCID 11430Potassium CarbonateHCID 132544-Phenoxyphenol

Product 1

HCID 21389473HCID 21389473, compoundYield 88.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

The compound of 4-phenoxyphenol (81.03 g, 435.5 mmol) was dissolved in 810 ml MEK at ambient temperature under Nitrogen. Powdered potassium carbonate (577.16 g, 4,176.27 mmol) was added followed by 1,3-dichloropropane (300.00 g, 2,655.1 mmol), and the resulting solution was heated to reflux for 15.5 hours. The solution was cooled to room temperature, filtered and washed with 750 ml MEK. The filtrate was concentrated under vacuum to give a crude orange liquid. The crude liquid was dissolved in 260 ml absolute MeOH at ambient temperature and stirred 5 minutes, which was then cooled in an ice/acetone/water bath for 1.5 hours. White precipitate was filtered off and washed with 480 ml cold absolute MeOH. The white solid was collected and dried under vacuum at 30° C. for 16 hours to afford about 81.87 g of compound (a).

Workup

  1. temperaturethe resulting solution was heated
  2. temperatureto reflux for 15.5 hours
  3. filtrationfiltered
  4. washwashed with 750 ml MEK
  5. concentrationThe filtrate was concentrated under vacuum
  6. customto give a crude orange liquid
  7. temperaturewhich was then cooled in an ice/acetone/water bath for 1.5 hours
  8. filtrationWhite precipitate was filtered off
  9. washwashed with 480 ml cold absolute MeOH
  10. customThe white solid was collected
  11. customdried under vacuum at 30° C. for 16 hours

Sources & evidence

ORD record
ord-1f299bbcd2c04e7d8e1914e7fe18cd3b
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Reaction notes

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