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

HRID 965512

Reaktionsgleichung

Reaktionsgleichung von HRID 965512
[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-743b2438b4464f77ba53c3d9fcfaa0c1
Quelldatensatz
uspto-grants-1998_06
Patentnummer
US05773594

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