Hydrochloric Acid → 2-(Naphthalen-1-yl)propane-1,3-diol

HRID 1613333

Reaktionsgleichung

Reaktionsgleichung von HRID 1613333
[C:1]1([CH:11]([C:17](OCC)=[O:18])[C:12](OCC)=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+].Cl.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>O1CCOCC1.O>[C:1]1([CH:11]([CH2:12][OH:13])[CH2:17][OH:18])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 14812Phosphorus oxide (P4O10)HCID 240505Diethyl 2-(1-naphthyl)malonateHCID 4311764Sodium borohydride

Produkt 1

HCID 146425962-(Naphthalen-1-yl)propane-1,3-diol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

50 g (175 mmol) of diethyl 2-(naphthalen-1-yl)propanedioate in 310 ml of dioxane and 300 ml of water are stirred at ambient temperature; an excess (2.2 mol, or 84 g) of sodium borohydride is then added in portions; the mixture is stirred for 8 h, and the products are left in contact for 2 days. The mixture is then hydrolysed, with stirring, while introducing crushed ice and 3N hydrochloric acid until an acidic pH is obtained. The mixture is extracted with diethyl ether, the organic phase is evaporated, and the residual oil is purified by chromatography on a silica gel column eluted with ethyl acetate. After evaporation and drying at 40° C. in the presence of phosphorus pentoxide, 18.5 g (91 mmol) of product are isolated. Melting point: 58-60° C.

Aufarbeitung

  1. waitthe products are left in contact for 2 days
  2. stirringhydrolysed, with stirring
  3. additionwhile introducing
  4. customis obtained
  5. extractionThe mixture is extracted with diethyl ether
  6. customthe organic phase is evaporated
  7. customthe residual oil is purified by chromatography on a silica gel column
  8. washeluted with ethyl acetate
  9. customAfter evaporation
  10. customare isolated

Quellen und Nachweise

ORD-Eintrag
ord-a6dd361719084b199d66c76a2f539123
Quelldatensatz
uspto-grants-1993_03
Patentnummer
US05192797

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