Water → 7-Hydroxy-6-methoxy-1-tetralone

HRID 856806

Reaktionsgleichung

Reaktionsgleichung von HRID 856806
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13]C)[C:9](=[O:15])[CH2:8][CH2:7][CH2:6]2.O>CC(O)=O.Br>[OH:13][C:12]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][C:9]2=[O:15])=[CH:4][C:3]=1[O:2][CH3:1]

Komponenten

5

Edukt 2

HCID 962WaterHCID 2668163,4-Dihydro-6,7-dimethoxy-1(2H)-naphthalenone

Produkt 1

HCID 3168407-Hydroxy-6-methoxy-1-tetraloneAusbeute 81,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 260Hydrogen BromideLösungsmittel

Versuchsvorschrift

A solution of 10 g (0.048 mole) of 6,7-dimethoxy-1-tetralone in 100 ml of HOAc and 100 ml of 48% aqueous HBr was heated at 95° C. for 7 hours. The reaction was cooled to room temperature and poured into water and extracted with EtOAc. The EtOAc layer was dried and evaporated to 12 g of crude product. Purification on 1200 g of silica gel eluting with 10% Et2O in CH2Cl2 gave 7.5 g of product. Mp 147-148° C. (literature mp 148-152° C., Journal of Organic Chemistry, 33, 1968, p. 508).

Aufarbeitung

  1. extractionextracted with EtOAc
  2. dry with materialThe EtOAc layer was dried
  3. customevaporated to 12 g of crude product
  4. customPurification on 1200 g of silica gel eluting with 10% Et2O in CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-621ac675adbd4667b8f184b2cac9b215
Quelldatensatz
uspto-grants-2006_12
Patentnummer
USRE039419E1

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