Dimethyl Sulfoxide → 1-Cyclohexyl-2-phenylpropan-1-one

HRID 275821

Reaktionsgleichung

Reaktionsgleichung von HRID 275821
CS(C)=O.[CH:5]1([CH:11]([OH:20])[CH:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH3:13])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.CCN(CC)CC>C(Cl)Cl>[C:14]1([CH:12]([C:11]([CH:5]2[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]2)=[O:20])[CH3:13])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 14812Phosphorus oxide (P4O10)HCID 120942241-Cyclohexyl-2-phenylpropanol

Produkt 1

HCID 142241151-Cyclohexyl-2-phenylpropan-1-oneAusbeute 85,437 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

DMSO (118 mL, 1.6674 mol) was added dropwise to a solution of 126.42 g (0.579 mol) of 1-cyclohexyl-2-phenylpropanol in 1737 mL of CH2Cl2 (cooled in a wet ice acetone bath). After 29 min, 147.93 g (1.0422 mol) of P2O5 was added. After 11 min, the cooling bath was removed. An aliquot quenched with Et3N showed complete reaction within 3 h at RT. The reaction mixture was cooled in a wet ice acetone bath. Et3N (282 mL, 2.0265 mol) was added dropwise to the cooled reaction mixture over a 30 min period. The cooling bath was removed and the mixture was stirred overnight at RT. The reaction mixture was quenched by dropwise addition of 500 mL of 3 N HCl (aq) (pH=0). After shaking in separatory funnel, the aqueous phase was removed. The organic phase was washed with 500 mL of 3 N HCl (aq) (pH=0), washed twice with 1 L of 10% K2CO3 (aq) (pH=12;12), washed three times with 500 mL of NaOCl (aq) solution, washed with 1L of water, washed with 1 L of 25% NaCl (aq), dried over MgSo4, gravity filtered and concentrated under vacuum with dry ice trap to collect Me2S. An amber oil of the title compound (107.01 g, 85.437%) was obtained; 1H NMR (d6-DMSO): δ 7.30-7.37 (m, 2H, phenyl CH), 7.21-7.28 (m, 3H, phenyl CH), 4.08 (q, J=6.9 Hz, 1H, —CH(CH3)Ph), 2.40-2.49 (m, 1H, cyclohexyl CH), 1.82-1.84 (m, 1H, cyclohexyl —CH2), 1.67-1.69 (m, 1H, cyclohexyl —CH2), 1.52-1.63 (m, 1H, cyclohexyl —CH2), 1.34-1.43 (m, 1H, cyclohexyl —CH2), 1.26 (d, J=6.9 Hz, 3H, —CH(CH3)Ph), 1.01-1.24 (m, 4H, cyclohexyl —CH2).

Aufarbeitung

  1. waitAfter 11 min
  2. customthe cooling bath was removed
  3. customAn aliquot quenched with Et3N showed complete reaction within 3 h at RT
  4. temperatureThe reaction mixture was cooled in a wet ice acetone bath
  5. customThe cooling bath was removed
  6. customThe reaction mixture was quenched by dropwise addition of 500 mL of 3 N HCl (aq) (pH=0)
  7. stirringAfter shaking in separatory funnel
  8. customthe aqueous phase was removed
  9. washThe organic phase was washed with 500 mL of 3 N HCl (aq) (pH=0)
  10. washwashed twice with 1 L of 10% K2CO3 (aq) (pH=12;12)
  11. washwashed three times with 500 mL of NaOCl (aq) solution
  12. washwashed with 1L of water
  13. washwashed with 1 L of 25% NaCl (aq)
  14. customdried over MgSo4, gravity
  15. filtrationfiltered
  16. concentrationconcentrated under vacuum with dry ice trap
  17. customto collect Me2S

Quellen und Nachweise

ORD-Eintrag
ord-63a9f733101444b6908fc2c31050e57e
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06353008B1

Verknüpfte Notizen

Wird geladen…