Water → Benzyl 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthylacetate

HRID 726469Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 726469
[H-].[Na+].[CH3:3][C:4]1([CH3:20])[CH2:13][CH2:12][C:11]([CH3:15])([CH3:14])[C:10]2[CH:9]=[C:8]([CH2:16][C:17]([OH:19])=[O:18])[CH:7]=[CH:6][C:5]1=2.[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.O>CN(C=O)C>[CH3:3][C:4]1([CH3:20])[CH2:13][CH2:12][C:11]([CH3:14])([CH3:15])[C:10]2[CH:9]=[C:8]([CH2:16][C:17]([O:19][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:18])[CH:7]=[CH:6][C:5]1=2

Komponenten

6

Edukt 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 181779322-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)acetic acid

Produkt 1

HCID 18792286Benzyl 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthylacetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

730 mg (0.024 mol) of sodium hydride (80 and 100 ml of DMF were introduced into a three-necked flank under a nitrogen stream. A solution of 5 g (0.02 mol) of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthylacetic acid in 40 ml of DMF was added dropwise and the mixture was stirred until the gaseous emission ceased. 2.9 ml (0.024 mol) of benzyl bromide were then added and the mixture was stirred at room temperature for 4 hours. The reaction medium was poured into water, and extracted with ethyl acetate. The organic phase was decanted off, dried over magnesium sulfate and evaporated. 6.7 g (100%) of the expected ester were recovered in the form of a slightly yellow oil.

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 4 hours
  2. extractionextracted with ethyl acetate
  3. customThe organic phase was decanted off
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. custom6.7 g (100%) of the expected ester were recovered in the form of a slightly yellow oil

Quellen und Nachweise

ORD-Eintrag
ord-ef9d103de7344601a737fc0d84aab076
Quelldatensatz
uspto-grants-1998_01
Patentnummer
US05709867

Notizen zur Reaktion

Wird geladen…