Ethylene Glycol → HCID 20536456, compound

HRID 1156111Notes

Reaction equation

HRID 1156111 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([NH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH2:27](O)[CH2:28][OH:29].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:9]=[C:8]([NH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH:7]=[CH:6][C:3]=1[CH:4]1[O:29][CH2:28][CH2:27][O:5]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 20536419HCID 20536419, compound

Product 1

HCID 20536456HCID 20536456, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-Fluoro-4-(hexadecylamino)benzaldehyde (1.7 g.) is dissolved in toluene (20 ml), and ethylene glycol (2.5 ml.) and p-toluenesulfonic acid (10 mg.) are added. The reaction mixture is heated under reflux for 16 hours while water is removed using a Dean-Stark trap. The reaction mixture is then cooled to room temperature, diluted with toluene (70 ml.), washed with aqueous sodium bicarbonate and then with water. The organic layer is separated dried over mangnesium sulfate, decolorized with charcoal and filtered through anhydrous magnesium silicate. Removal of the solvent in vacuo gives a light yellow solid which is recrystallized from hexane to yield 2-[2-fluoro-4-(hexadecylamino)phenyl]-1,3-dioxolane.

Workup

  1. temperatureThe reaction mixture is heated
  2. customis removed
  3. additiondiluted with toluene (70 ml.)
  4. washwashed with aqueous sodium bicarbonate
  5. customThe organic layer is separated
  6. dry with materialdried over mangnesium sulfate
  7. filtrationfiltered through anhydrous magnesium silicate
  8. customRemoval of the solvent in vacuo
  9. customgives a light yellow solid which
  10. customis recrystallized from hexane

Sources & evidence

ORD record
ord-426746db10f94009b760955696d0b793
Source dataset
uspto-grants-1982_06
Patent number
US04333940

Reaction notes

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