Hydrochloric Acid → Allyl 4-mesyloxymethyl-1-methyl-1-cyclohexanecarboxylate

HRID 2225500

Reaktionsgleichung

Reaktionsgleichung von HRID 2225500
[S:1](Cl)([CH3:4])(=[O:3])=[O:2].[OH:6][CH2:7][CH:8]1[CH2:13][CH2:12][C:11]([CH3:20])([C:14]([O:16][CH2:17][CH:18]=[CH2:19])=[O:15])[CH2:10][CH2:9]1.Cl>N1C=CC=CC=1>[S:1]([O:6][CH2:7][CH:8]1[CH2:13][CH2:12][C:11]([CH3:20])([C:14]([O:16][CH2:17][CH:18]=[CH2:19])=[O:15])[CH2:10][CH2:9]1)([CH3:4])(=[O:3])=[O:2]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 31297Methanesulfonyl chlorideHCID 19004756Allyl 4-hydroxymethyl-1-methyl-1-cyclohexanecarboxylate

Produkt 1

HCID 19004719Allyl 4-mesyloxymethyl-1-methyl-1-cyclohexanecarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

4.5 ml of mesyl chloride was added to a solution of 2.1 g of allyl 4-hydroxymethyl-1-methyl-1-cyclohexanecarboxylate (Example 44) in 50 ml of pyridine. The solution was reacted for 3 hours at room temperature. After reaction, 100 ml of 2N hydrochloric acid was added to the reaction solution. The solution was extracted three times with 30 ml of ethyl acetate. The organic layer obtained was washed once with an aqueous sodium hydrogencarbonate solution and twice with an aqueous sodium chloride solution, and was dried over magnesium sulfate. Thereafter, the solvent was removed in vacuo. The oily substance obtained was subjected to column chromatography using 20 g of silica gel. From the fraction eluted with hexane and ethyl acetate=2:1, the solvent was removed in vacuo, yielding 2 g of allyl 4-mesyloxymethyl-1-methyl-1-cyclohexanecarboxylate as a pale yellow oil, which had the following physiochemical properties:

Aufarbeitung

  1. customThe solution was reacted for 3 hours at room temperature
  2. additionwas added to the reaction solution
  3. extractionThe solution was extracted three times with 30 ml of ethyl acetate
  4. customThe organic layer obtained
  5. washwas washed once with an aqueous sodium hydrogencarbonate solution and twice with an aqueous sodium chloride solution
  6. dry with materialwas dried over magnesium sulfate
  7. customThereafter, the solvent was removed in vacuo
  8. customThe oily substance obtained
  9. washFrom the fraction eluted with hexane and ethyl acetate=2:1
  10. customthe solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6e2a9963de5a47b38fcc748e623fe06d
Quelldatensatz
uspto-grants-1994_09
Patentnummer
US05344845

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