Water → 1,4-Benzenedimethanol, 2,5-difluoro-

HRID 1391073

Reaktionsgleichung

Reaktionsgleichung von HRID 1391073
[F:1][C:2]1[C:10](F)=[C:9]([C:12](O)=[O:13])[C:8]([F:15])=[C:7](F)[C:3]=1[C:4](O)=[O:5].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].O>O1CCCC1.CCOCC>[OH:5][CH2:4][C:3]1[CH:7]=[C:8]([F:15])[C:9]([CH2:12][OH:13])=[CH:10][C:2]=1[F:1]

Komponenten

7

Edukt 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 695492,3,5,6-Tetrafluoroterephthalic acidHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 226301921,4-Benzenedimethanol, 2,5-difluoro-

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
10 °C

Versuchsvorschrift

A solution of 63.2 g (0.265 mols of 2,3,5,6-tetrafluoroterephthalic acid (m.p. 268 - 271° C., obtainable from Pierce-Chemical, Rockford, Ill., U.S.A., in 450 ml of tetrahydrofuran are introduced in the course of 1 hour into a solution of 40.3 g (1.06 mols) of lithium aluminium hydride in 1200 ml of tetrahydrofuran. The reaction mixture is refluxed for 24 hours, then cooled to 10° C. and treated carefully with 40 ml of 15% sodium hydroxide solution and finally with 120ml of water. The white precipitate is filtered off, washed with 500 ml of tetrahydrofuran, and the clear filtrate concentrated at 60° C. under vacuum. 37.9 g of slightly yellow-colored crystals are obtained. This-layer chromatography reveals them to be a mixture of at least three substances. To isolate a unitary substance, the batch is dissolved in 500 ml of ether, 2.8 g of insoluble constituents are removed by filtration, and the ethereal solution concentrated to one-third its volume. It is then treated with 35 ml of pentane and cooled to 10° C., white crystals precipitating. After two recrystallizations from ether+pentane, 3.4 g of fine needles are obtained which melt at 107-109° C.

Aufarbeitung

  1. temperatureThe reaction mixture is refluxed for 24 hours
  2. filtrationThe white precipitate is filtered off
  3. washwashed with 500 ml of tetrahydrofuran
  4. concentrationthe clear filtrate concentrated at 60° C. under vacuum
  5. custom37.9 g of slightly yellow-colored crystals are obtained
  6. additiona mixture of at least three substances
  7. customTo isolate a unitary substance
  8. custom2.8 g of insoluble constituents are removed by filtration
  9. concentrationthe ethereal solution concentrated to one-third its volume
  10. additionIt is then treated with 35 ml of pentane
  11. temperaturecooled to 10° C.
  12. customwhite crystals precipitating
  13. customAfter two recrystallizations from ether+pentane, 3.4 g of fine needles
  14. customare obtained which melt at 107-109° C.

Quellen und Nachweise

ORD-Eintrag
ord-aac97f29ef7549e5aea8b879f19768d8
Quelldatensatz
uspto-grants-1979_02
Patentnummer
US04140843

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