Sulfuric Acid → 4-Hydroxyindan

HRID 59603

Reaktionsgleichung

Reaktionsgleichung von HRID 59603
N[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][CH2:6]2.S(=O)(=O)(O)[OH:12].N([O-])=O.[Na+].NC(N)=O>O>[OH:12][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][CH2:6]2

Komponenten

6

Edukt 4

HCID 1118Sulfuric AcidHCID 1176UreaHCID 1225694-AminoindanHCID 23668193Sodium Nitrite

Produkt 1

HCID 742334-Hydroxyindan

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel3×

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

4-Aminoindan (3.0 g) was added to a solution of concentrated sulphuric acid (2.4 mL) in water (15 mL). More water (15 mL) was added and the mixture cooled to 5° C. A solution of sodium nitrite (1.71 g) in water (4.5 mL) was added portionwise to the mixture while maintaining the temperature below 5° C. After addition was complete the mixture was allowed to warm to room temperature and urea (0.29 g) was added. The mixture was stirred for a further 5 minutes before being heated at 45° C. for 30 minutes. The mixture was then cooled to room temperature and extracted with ethyl acetate. The combined organic extracts were washed with 2M aqueous sodium hydroxide (2×100 mL) and these aqueous extracts were then acidified with hydrochloric acid and extracted with ethyl acetate (3×100 mL). The combined organic extracts were then washed with brine and dried (Na2SO4) before being concentrated in vacuo. The resulting crude product was chromatographed over silica gel. Elution with ethyl acetate/hexanes (1:7) gave 4-hydroxyindan as an orange oil (1.0 g).

Aufarbeitung

  1. temperaturewhile maintaining the temperature below 5° C
  2. additionAfter addition
  3. temperatureto warm to room temperature
  4. temperaturebefore being heated at 45° C. for 30 minutes
  5. temperatureThe mixture was then cooled to room temperature
  6. extractionextracted with ethyl acetate
  7. washThe combined organic extracts were washed with 2M aqueous sodium hydroxide (2×100 mL)
  8. extractionextracted with ethyl acetate (3×100 mL)
  9. washThe combined organic extracts were then washed with brine
  10. dry with materialdried (Na2SO4)
  11. concentrationbefore being concentrated in vacuo
  12. customThe resulting crude product was chromatographed over silica gel
  13. washElution with ethyl acetate/hexanes (1:7)

Quellen und Nachweise

ORD-Eintrag
ord-4dfbcf84f32b427b82a7260df567ac29
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440926B2

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