Formaldehyde → 2-(4H-benzo[d][1,3]dioxin-6-yl)acetonitrile

HRID 1255576

Reaktionsgleichung

Reaktionsgleichung von HRID 1255576
OC1C=CC([CH2:8][C:9]#[N:10])=CC=1.[CH2:11]=[O:12].[OH2:13].[C:14]1([CH3:24])[CH:19]=[CH:18][C:17](S(O)(=O)=O)=[CH:16][CH:15]=1>C1(C)C=CC=CC=1>[O:12]1[C:15]2[CH:16]=[CH:17][C:18]([CH2:8][C:9]#[N:10])=[CH:19][C:14]=2[CH2:24][O:13][CH2:11]1

Komponenten

5

Edukt 3

HCID 712FormaldehydeHCID 265484-Hydroxybenzyl cyanideHCID 521998p-Toluenesulfonic acid monohydrate

Produkt 1

HCID 591662212-(4H-benzo[d][1,3]dioxin-6-yl)acetonitrileAusbeute 9.757,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of (4-hydroxyphenyl)acetonitrile (17.3 g, 0.13 mol) in toluene (350 mL) were added paraformaldehyde (39.0 g, 0.43 mmol) and toluene-4-sulfonic acid monohydrate (2.5 g, 13 mmol) at room temperature. The reaction mixture was heated at reflux for 1 hour. Toluene was removed by evaporation. Water (150 mL) and ethyl acetate (150 mL) were added. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organics were washed with brine, dried over Na2SO4 and evaporated under vacuum. The residue was separated by preparative HPLC to give 2-(4H-benzo[d][1,3]dioxin-6-yl)acetonitrile (7.35 g, 32%). 1H NMR (400 MHz, CDCl3) δ 7.07-7.11 (m, 1H), 6.95-6.95 (m, 1H), 6.88 (d, J=11.6 Hz, 1H), 5.24 (s, 2H), 4.89 (s, 2H), 3.67 (s, 2H).

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 1 hour
  3. customToluene was removed by evaporation
  4. additionWater (150 mL) and ethyl acetate (150 mL) were added
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted with ethyl acetate
  7. washThe combined organics were washed with brine
  8. dry with materialdried over Na2SO4
  9. customevaporated under vacuum
  10. customThe residue was separated by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-9cd77dabb755410d89ed640c743b7fc9
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08461156B2

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