Methyl 4-Formylbenzoate → 1-(4-Carbomethoxyphenyl)-4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-butane-1,4-dione

HRID 346274

Reaktionsgleichung

Reaktionsgleichung von HRID 346274
Cl[CH2:2][CH2:3][C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[C:12]([CH3:17])([CH3:16])[CH2:11][CH2:10][C:9]2([CH3:19])[CH3:18])=[O:5].[CH:20]([C:22]1[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][CH:23]=1)=[O:21]>[Cl-].C([N+]1C(C)=C(CCO)SC=1)C1C=CC=CC=1.CN(C)C=O>[C:26]([C:25]1[CH:30]=[CH:31][C:22]([C:20](=[O:21])[CH2:2][CH2:3][C:4]([C:6]2[CH:15]=[CH:14][C:13]3[C:12]([CH3:17])([CH3:16])[CH2:11][CH2:10][C:9]([CH3:19])([CH3:18])[C:8]=3[CH:7]=2)=[O:5])=[CH:23][CH:24]=1)([O:28][CH3:29])=[O:27]

Komponenten

5

Edukt 2

HCID 15294Methyl 4-FormylbenzoateHCID 147265116-(3-Chloropropionyl)-1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalene

Produkt 1

HCID 147264921-(4-Carbomethoxyphenyl)-4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-butane-1,4-dioneAusbeute 45,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 28333523-Benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chlorideKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

5.6 g (0.02 mole) of 6-(3-chloropropionyl)-1,2,3,4-tetrahydro-1,1,4,4-tetramethylnapthalene and 3.3 were stirred for 1 hour at room temperature. Thereafter, a solution of 3.6 g (0.025 mole) of methyl 4-formylbenzoate and 1 g of 3-benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chloride in 10 ml of dimethylformamide was added dropwise. Stirring was continued for 1 hour, after which the mixture was poured onto ice/water and extracted twice with ethyl acetate, and the combined organic extracts were washed several times with water, dried over magnesium sulfate and evaporated down. 3.7 g of 1-(4-carbomethoxyphenyl)-4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-butane-1,4-dione of melting point 139°-141° C. were obtained from the residue (6.4 g) after recrystallization from ethanol. 2-(4-Carbomethoxyphenyl)-5-(5,6,7,8-tetrahy-dro-5,5,8,8-tetramethyl-2-naphthalenyl)-thiophene:

Aufarbeitung

  1. additionafter which the mixture was poured onto ice/water
  2. extractionextracted twice with ethyl acetate
  3. washthe combined organic extracts were washed several times with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated down

Quellen und Nachweise

ORD-Eintrag
ord-9d07dbe3191c4f18ad954efa97c1f00e
Quelldatensatz
uspto-grants-1991_10
Patentnummer
US05061705

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