Ethylene Glycol → HCID 18931340, compound

HRID 1598990Notes

Reaction equation

HRID 1598990 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]([C:8]1[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=1[O:15][CH3:16])=[O:7].[CH2:17](O)[CH2:18][OH:19].C1(C)C=CC=CC=1>C1C2C(=CC=CC=2)C=CC=1S(O)(=O)=O.O>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1([C:8]2[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=2[O:15][CH3:16])[O:19][CH2:18][CH2:17][O:7]1

Participants

6

Reactant 3

HCID 174Ethylene Glycol2×HCID 1140TolueneHCID 18931279HCID 18931279, compound

Product 1

HCID 18931340HCID 18931340, compoundYield 95.4%

Reagents, catalysts & solvents 2

HCID 84202-Naphthalenesulfonic acidCatalystHCID 962WaterSolvent

Procedure

A mixture of 5-chloro-1-(5-chloro-2-methoxyphenyl)-1-pentanone (2 g, 7.66 mmol), prepared as in Example 7, ethylene glycol (1.25 g, 20 mmol), 2-napthalenesulfonic acid (50 mg, 0.24 mmol) and toluene (approximately 80 mL) was heated 4-5 hours at reflux (removing water with a Dean-Stark trap) and then additional ethylene glycol (1 g, 16 mmol) was added. The mixture was heated approximately 16 hours at reflux and then washed with saturated sodium bicarbonate, water (3×) and brine (1×), dried (K2 CO3), filtered and concentrated to give 5-chloro-1-(5-chloro-2-methoxyphenyl)-1,1-ethylenedioxypentane (2.23 g, 7.31 mmol) as an oil.

Workup

  1. temperaturewas heated 4-5 hours
  2. temperatureat reflux (
  3. additionwas added
  4. temperatureThe mixture was heated approximately 16 hours
  5. temperatureat reflux
  6. washwashed with saturated sodium bicarbonate, water (3×) and brine (1×)
  7. customdried (K2 CO3)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-c680f4807c8b464d8021c91f21e489d8
Source dataset
uspto-grants-1998_04
Patent number
US05739336

Reaction notes

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