Ethylene Glycol → HCID 13478167, compound

HRID 2118527Notes

Reaction equation

HRID 2118527 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH3:14])[C:9](=[O:15])[CH2:8][C:7]2([CH3:17])[CH3:16])(=[O:3])[CH3:2].[CH2:18](O)[CH2:19][OH:20].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1.C(OCC)(=O)C>[CH3:14][N:10]1[C:11]2[C:6](=[CH:5][C:4]([C:1]3([CH3:2])[O:20][CH2:19][CH2:18][O:3]3)=[CH:13][CH:12]=2)[C:7]([CH3:17])([CH3:16])[CH2:8][C:9]1=[O:15]

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 134781666-Acetyl-1,4,4-trimethyl-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 13478167HCID 13478167, compoundYield 94.1%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8857Ethyl AcetateSolvent

Procedure

5.0 g of 6-acetyl-3,4-dihydro-1,4,4-trimethyl-2(1H)-quinolinone were dissolved in 200 ml of benzene and, after the addition of 2.1 g of ethylene glycol and a few crystals of p-toluenesulphonic acid, the mixture was boiled under a water separator for 5 hours. After cooling, the mixture was diluted with ethyl acetate, washed with dilute sodium hydrogen carbonate solution, dried and evaporated. There were obtained 5.6 g of 3,4-dihydro-1,4,4-trimethyl-6-(2-methyl-1,3-dioxolan-2-yl)-2(1H)-quinolinone in the form of a colourless oil which solidified upon standing in a refrigerator; melting point 81°-83° C. This compound was used in the next step without further purification.

Workup

  1. customfor 5 hours
  2. temperatureAfter cooling
  3. washwashed with dilute sodium hydrogen carbonate solution
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-d54b1306e9bf4655bc5ed60e47142826
Source dataset
uspto-grants-1987_07
Patent number
US04678793

Reaction notes

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