Diethylene Glycol → 2-[2-[4-[1,1,2,2-Tetrafluoro-2-[4-[2-(2-hydroxyethoxy)ethoxy]phenyl]ethyl]phenoxy]ethoxy]ethanol

HRID 978813Notes

Reaction equation

HRID 978813 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:20])([F:19])[C:9]([C:12]2[CH:17]=[CH:16][C:15](F)=[CH:14][CH:13]=2)([F:11])[F:10])=[CH:4][CH:3]=1.[CH2:21]([OH:27])[CH2:22][O:23][CH2:24][CH2:25][OH:26]>>[OH:27][CH2:21][CH2:22][O:23][CH2:24][CH2:25][O:26][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:20])([F:19])[C:9]([C:12]2[CH:17]=[CH:16][C:15]([O:27][CH2:21][CH2:22][O:23][CH2:24][CH2:25][OH:26])=[CH:14][CH:13]=2)([F:11])[F:10])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 8117Diethylene GlycolHCID 111737881,1'-(1,1,2,2-Tetrafluoroethane-1,2-diyl)bis(4-fluorobenzene)

Product 1

HCID 136910872-[2-[4-[1,1,2,2-Tetrafluoro-2-[4-[2-(2-hydroxyethoxy)ethoxy]phenyl]ethyl]phenoxy]ethoxy]ethanol

Conditions

Temperature
150 °C

Procedure

700 ml of diethylene glycol and 65 g of 1,2-bis(4-fluorophenyl)-1,1,2,2-tetrafluoroethane* are heated to 130° C. in a stirred flask and 57 g of potassium tert.-butylate are added in portions. The mixture is then heated to 150° C. and stirred at this temperature for 2 hours. The mixture is cooled, poured onto 4 liters of ice-water and mixed thoroughly with a homogenizer (Ultraturax), until crystals precipitate. The precipitate is filtered off with suction, stirred again with 3 liters of water, acidified with hydrochloric acid, filtered off with suction again, dried and recrystallized from toluene.

Workup

  1. temperatureThe mixture is cooled
  2. additionmixed thoroughly with a homogenizer (Ultraturax), until crystals
  3. customprecipitate
  4. filtrationThe precipitate is filtered off with suction
  5. stirringstirred again with 3 liters of water
  6. filtrationfiltered off with suction again
  7. customdried
  8. customrecrystallized from toluene

Sources & evidence

ORD record
ord-bfcb636da48d427bae6b4c10d4bbd218
Source dataset
uspto-grants-1987_05
Patent number
US04665217

Reaction notes

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