Hydrochloric Acid → 4-Hydroxy-7-methylcoumarin

HRID 260439

Reaktionsgleichung

Reaktionsgleichung von HRID 260439
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:10])=[O:9])=[C:4]([OH:11])[CH:3]=1.[H-].[Na+].[CH2:14]([O:16]C(=O)OCC)C.Cl>C1C=CC=CC=1>[OH:9][C:8]1[C:5]2[C:4](=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=2)[O:11][C:14](=[O:16])[CH:10]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 7766Diethyl Carbonate2×HCID 24758Sodium hydride2×HCID 813382'-Hydroxy-4'-methylacetophenone

Produkt 1

HCID 546853074-Hydroxy-7-methylcoumarinAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel3×

Versuchsvorschrift

A solution of 42 g (0.28 mol) of 2-hydroxy-4-methylacetophenone in benzene (150 mL) was added over 30 min. to a suspension of NaH (50% oil), 30 g, 0.63 mol) in 400 mL of benzene at reflux. Then, diethylcarbonate (67.8 mL, 0.56 mol) in benzene (500 mL) was added over 15 min. The reaction mixture was refluxed for 16 s h and more NaH (13 g, 0.28 mol) was added followed by more diethylcarbonate (33 g, 0.28 mol). After another 6 h at reflux the reaction mixture was cooled to r.t. and HCl (2N) was added (1.5 L) to form a white precipitate. The solid was then filtered and added to a solution of NaOH (4N) (800 mL). The resulting basic solution was then extracted with Et2O (2×500 mL) and the basic solution acidified with HCl conc. to give a white solid which after filtration and dried gave 38.7 g (79%) of the title compound.

Aufarbeitung

  1. temperatureat reflux
  2. additionwas added
  3. temperatureAfter another 6 h at reflux the reaction mixture
  4. customto form a white precipitate
  5. filtrationThe solid was then filtered
  6. additionadded to a solution of NaOH (4N) (800 mL)
  7. extractionThe resulting basic solution was then extracted with Et2O (2×500 mL)
  8. customto give a white solid which
  9. filtrationafter filtration
  10. customdried

Quellen und Nachweise

ORD-Eintrag
ord-52a707541e6549d5bb29afdd5104a8e9
Quelldatensatz
uspto-grants-1996_06
Patentnummer
US05527827

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