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Diethyl Malonate → 3-[3-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)acryloyloxy]benzoic acid

HRID 2268211
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Reaktionsgleichung

Reaktionsgleichung von HRID 2268211
[H-].[Na+].C1COCC1.C(OCC)(=O)CC(OCC)=O.[CH3:19][C:20]1([CH3:49])[CH2:29][CH2:28][C:27]([CH3:31])([CH3:30])[C:26]2[CH:25]=[C:24]([CH:32]=[CH:33][C:34]([O:36][C:37]3[CH:38]=[C:39]([CH:46]=[CH:47][CH:48]=3)[C:40]([O:42]CC=C)=[O:41])=[O:35])[CH:23]=[CH:22][C:21]1=2>O>[CH3:19][C:20]1([CH3:49])[CH2:29][CH2:28][C:27]([CH3:30])([CH3:31])[C:26]2[CH:25]=[C:24]([CH:32]=[CH:33][C:34]([O:36][C:37]3[CH:38]=[C:39]([CH:46]=[CH:47][CH:48]=3)[C:40]([OH:42])=[O:41])=[O:35])[CH:23]=[CH:22][C:21]1=2
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Komponenten

6

Edukt 4

HCID 7761Diethyl MalonateHCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 70213311Allyl 3-[3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)acryloyloxy]benzoate

Produkt 1

HCID 702158333-[3-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)acryloyloxy]benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

210 mg (6.8 mmol) of sodium hydride (80% in oil) and 15 ml of THF are introduced into a round-bottomed flask under a stream of nitrogen. 1 ml (6.8 mmol) of diethyl malonate is then added dropwise and the mixture is stirred until the evolution of gas has ceased. This solution is introduced dropwise into a mixture of 2.6 g (6.2 mmol) of allyl 3-[3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)acryloyloxy]-benzoate, 50 ml of THF and 400 mg of tetrakis-(triphenylphosphine)palladium(0) and the mixture is stirred at room temperature for three hours. The reaction medium is poured into water and extracted with ethyl ether, and the organic phase is separated out after settling has taken place, dried over magnesium sulphate and evaporated. The residue obtained is purified by chromatography on a column of silica eluted with a mixture of ethyl ether and hexane (50/50). After evaporating the solvents, 1.5 g (64%) of 3-[3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)acryloyloxy]-benzoic acid, with a melting point of 134-5° C., are collected.

Aufarbeitung

  1. stirringthe mixture is stirred at room temperature for three hours
  2. extractionextracted with ethyl ether
  3. customthe organic phase is separated out after settling
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. customThe residue obtained
  7. customis purified by chromatography on a column of silica
  8. washeluted with a mixture of ethyl ether and hexane (50/50)
  9. customAfter evaporating the solvents, 1.5 g (64%) of 3-[3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)acryloyloxy]-benzoic acid
  10. customwith a melting point of 134-5° C., are collected

Quellen und Nachweise

ORD-Eintrag
ord-c9b5c5a48b184ae58264c72f3a8892db
Quelldatensatz
uspto-grants-2001_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06326510B1

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