Ethylene Glycol → HCID 20298538, compound

HRID 1389149Notes

Reaction equation

HRID 1389149 reaction equation
[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[CH:5]=[C:4]([CH2:14][CH2:15][C:16](=[O:18])[CH3:17])[CH:3]=1.[CH2:19](O)[CH2:20][OH:21].C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>C1C=CC=CC=1.O>[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[CH:5]=[C:4]([CH2:14][CH2:15][C:16]2([CH3:17])[O:21][CH2:20][CH2:19][O:18]2)[CH:3]=1

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 9859690HCID 9859690, compound

Product 1

HCID 20298538HCID 20298538, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

4-(4-Fluoro-6-methoxy-2-naphthyl)butan-2-one (4.2 g), ethane-1,2-diol (30 ml) and toluene-4-sulphonic acid (0.2 g) were heated under reflux in benzene for 18 hours with continuous removal of water by means of a Dean-Stark trap. The solution was then cooled to room temperature and sodium hydrogen carbonate solution was added. The aqueous layer was washed with ether. The combined organic layers were washed with water and dried over anhydrous sodium sulphate. Evaporation of the solvent under reduced pressure gave a crude product which was dissolved in 60-80 petroleum ether. The precipitated impurities were removed by filtration and the solvent was removed under reduced pressure to give a yellow oil which was triturated with cold 40-60 petroleum ether to give the title compound as pale yellow crystals (2.6 g., 53%; m.p. 51°-53°).

Workup

  1. washThe aqueous layer was washed with ether
  2. washThe combined organic layers were washed with water
  3. dry with materialdried over anhydrous sodium sulphate
  4. customEvaporation of the solvent under reduced pressure
  5. customgave a crude product which
  6. customThe precipitated impurities were removed by filtration
  7. customthe solvent was removed under reduced pressure
  8. customto give a yellow oil which
  9. customwas triturated with cold 40-60 petroleum ether

Sources & evidence

ORD record
ord-f7985c8306e8415bb659287b476995df
Source dataset
uspto-grants-1981_01
Patent number
US04243682

Reaction notes

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