Sodium Phosphate, Dibasic → Octanedial

HRID 1531593Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1531593
[CH2:1]([OH:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][OH:9].P([O-])([O-])([O-])=O.[Na+].[Na+].[Na+].P(O)([O-])([O-])=O.[Na+].[Na+].Cl[O-].[Na+]>C(Cl)Cl.O.CC1(C)N([O])C(C)(C)CCC1.[Br-].[K+]>[CH:1](=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH:8]=[O:9]

Komponenten

9

Edukt 4

HCID 24203Sodium Phosphate, DibasicHCID 24243Trisodium PhosphateHCID 694201,8-OctanediolHCID 23665760Sodium Hypochlorite

Produkt 1

HCID 69491OctanedialAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 253877Potassium BromideKatalysatorHCID 2724126TempoKatalysatorHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a heterogeneous mixture of octane-1,8-diol (94.64 g, 0.648 mole), TEMPO (5.08 g, 0.038 mole, available from Aldrich Chemical Company, Milwaukee, Wis.), potassium bromide (3.90 g, 0.033 mole), sodium phosphate (7.80 g, 0.065 mole), disodium phosphate (9.24 g, 0.065 mole) in methylene chloride (1.3 L) and water (500 ml) was added dropwise 12% aqueous sodium hypochlorite (1,225 g) slowly over 2 hours while maintaining the temperature below 35° C. The reaction was stirred for an additional 30 minutes and the two layers were separated. The aqueous layer was extracted with methylene chloride and combined with the organic layer. The combined organic layer was washed with saturated aqueous sodium bicarbonate, saturated aqueous sodium chloride and water. The organic fraction was dried over sodium sulfate, filtered and evaporated. The material was vacuum distilled 82-84° C./0.5 mm Hg to afford octane-1,8-dial (92 g, 100% yield). C8H14O2 (142.20 g/mole). bp: 82° C./0.55 mm Hg. 1HNMR (500 MHz, CDCl3): 1.35 (m, 4H), 1.63 (m, 4H), 2.43 (m, 4H), 9.76 (t, 2H) ppm. 13CNMR (125 MHz, CDCl3): 21.8, 28.9, 43.8, 202.7 ppm. IR (νmax(cm−1)): 2940, 2860, 2740, 1725, 1460, 1420, 1400. MS (m/z): 24(M-18), 98, 95, 81, 67, 57, 54, 44, 41.

Aufarbeitung

  1. temperaturewhile maintaining the temperature below 35° C
  2. customthe two layers were separated
  3. extractionThe aqueous layer was extracted with methylene chloride
  4. washThe combined organic layer was washed with saturated aqueous sodium bicarbonate, saturated aqueous sodium chloride and water
  5. dry with materialThe organic fraction was dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. distillationdistilled 82-84° C./0.5 mm Hg

Quellen und Nachweise

ORD-Eintrag
ord-ea56cafbc7cc4cd7b45db35a949affc7
Quelldatensatz
uspto-grants-2001_03
Patentnummer
US06200254B1

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