2-Methylbenzenesulfonic acid hydrate → 5-(4-Chlorobenzyl)-2-chloromethyl-2-methyl-cyclopentanone

HRID 922739Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 922739
COC([C:5]1([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[CH2:9][CH2:8][C:7]([CH2:11][Cl:12])([CH3:10])[C:6]1=[O:13])=O.O.C1(C)C(S(O)(=O)=O)=CC=CC=1>O>[Cl:21][C:18]1[CH:17]=[CH:16][C:15]([CH2:14][CH:5]2[C:6](=[O:13])[C:7]([CH2:11][Cl:12])([CH3:10])[CH2:8][CH2:9]2)=[CH:20][CH:19]=1

Komponenten

4

Edukt 2

HCID 124969952-Methylbenzenesulfonic acid hydrateHCID 867182561-(4-Chlorobenzyl)-3-chloromethyl-3-methyl-2-oxo-cyclopentancarboxylic acid methyl ester

Produkt 1

HCID 867182595-(4-Chlorobenzyl)-2-chloromethyl-2-methyl-cyclopentanoneAusbeute 91,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To 1.00 g of Compound 3-1-3 synthesized in Production Example 4, 0.578 g of toluenesulfonic acid monohydrate and 100 mg of water were added, and the resulting mixture was stirred in an oil bath of 120° C. for 1.5 hours. After the reaction, water was added to the reaction solution thus obtained, and extraction with ethyl acetate was then carried out. The extract was washed with an aqueous solution of sodium hydrogen carbonate and saturated brine. After the organic layer was dried over anhydrous sodium sulfate, the solvent was distilled away. The residue was purified by silica gel column chromatography to obtain 752 mg of Compound 4-1-3.

Aufarbeitung

  1. additionwere added
  2. additionwas added to the reaction solution
  3. customthus obtained
  4. extractionextraction with ethyl acetate
  5. washThe extract was washed with an aqueous solution of sodium hydrogen carbonate and saturated brine
  6. dry with materialAfter the organic layer was dried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled away
  8. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-e83c17d032ee49ad9eed6a208d26cd9d
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09278966B2

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