Sulfuric Acid → 3-(2-Hydroxybenzylidene)dihydrofuran-2(3h)-one

HRID 460655Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 460655
[CH:1](=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[C:10]1(=[O:15])[O:14][CH2:13][CH2:12][CH2:11]1.C[O-].[Na+].S(=O)(=O)(O)O>C1(C)C=CC=CC=1>[OH:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[CH:1]=[C:11]1[CH2:12][CH2:13][O:14][C:10]1=[O:15]

Komponenten

6

Edukt 4

HCID 1118Sulfuric AcidHCID 6998SalicylaldehydeHCID 7302Gamma-ButyrolactoneHCID 10942334Sodium Methoxide

Produkt 1

HCID 2297583-(2-Hydroxybenzylidene)dihydrofuran-2(3h)-oneAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

Salicylaldehyde (293 g) and γ-butyrolactone (413 g) were dissolved in toluene (2.4 L) and the solution was cooled to not more than 3° C. in an ice-salt bath. Thereto was added sodium methoxide (324 g) over 20 min. The temperature of the reaction mixture rose to 24° C. After stirring at room temperature for 3 hr, the mixture was stirred for 45 min under heating at 60–65° C. The reaction mixture was cooled again in an ice-bath and 10% sulfuric acid (2.51 ml) was added dropwise. The obtained white suspension was filtrated, washed with water and dried to give the title compound (324 g), melting point 162–164° C.

Aufarbeitung

  1. temperaturethe solution was cooled to not more than 3° C. in an ice-salt bath
  2. customrose to 24° C
  3. stirringthe mixture was stirred for 45 min
  4. temperatureunder heating at 60–65° C
  5. temperatureThe reaction mixture was cooled again in an ice-bath
  6. filtrationThe obtained white suspension was filtrated
  7. washwashed with water
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-b60537c0b894480fb6c9d2d2d501c215
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07196199B2

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