Water → 3,4-Dihydro-4,4-dimethyl-1(carboethoxymethyl)-6-acetyl-naphthalene

HRID 611038

Reaktionsgleichung

Reaktionsgleichung von HRID 611038
[CH3:1][C:2]1([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[C:13](O)([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:12][CH2:11][C:10]3([CH3:25])[CH3:24])OCC[O:3]1.CC1C=CC(S(O)(=O)=O)=CC=1.O>C1C=CC=CC=1>[CH3:24][C:10]1([CH3:25])[C:9]2[C:14](=[CH:15][CH:16]=[C:7]([C:2](=[O:3])[CH3:1])[CH:8]=2)[C:13]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:12][CH2:11]1

Komponenten

5

Edukt 3

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 18415063(+/-) 6-(2-Methyl-1,3-dioxolan-2-yl)-1,2,3,4-tetrahydro-4,4-dimethyl-1-hydroxy-1-(carboethoxymethyl)-naphthalene

Produkt 1

HCID 225715193,4-Dihydro-4,4-dimethyl-1(carboethoxymethyl)-6-acetyl-naphthalene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

A solution of (+/-) 6-(2-methyl-1,3-dioxolan-2-yl)-1,2,3,4-tetrahydro-4,4-dimethyl-1-hydroxy-1-(carboethoxymethyl)-naphthlene ((Compound D16, 321 mg, 0.90 mmol) and catalytic amount of TsOH in 20 ml of benzene was refluxed for 12 h. During the reaction the water generated from the reaction was periodically removed by a Dean-Stark trap. The solvent was removed and the residue was purified by column chromatography (silica, ethyl acetate/hexane (1/3)) to give the title compound as an oil (215 mg).

Aufarbeitung

  1. customwas periodically removed by a Dean-Stark trap
  2. customThe solvent was removed
  3. customthe residue was purified by column chromatography (silica, ethyl acetate/hexane (1/3))

Quellen und Nachweise

ORD-Eintrag
ord-898661849e1f44d7a3c9e8d03537c50b
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US05998655

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