Hydrochloric Acid → (4-Formyl-cyclohexyl)-methyl-carbamic acid benzyl ester

HRID 25656Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 25656
[CH2:1]([O:8][C:9](=[O:21])[N:10]([CH:12]1[CH2:17][CH2:16][C:15](=[CH:18][O:19]C)[CH2:14][CH2:13]1)[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>C1COCC1>[CH2:1]([O:8][C:9](=[O:21])[N:10]([CH:12]1[CH2:17][CH2:16][CH:15]([CH:18]=[O:19])[CH2:14][CH2:13]1)[CH3:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 69194804(4-Methoxymethylene-cyclohexyl)-methyl-carbamic acid benzyl ester

Produkt 1

HCID 86584993(4-Formyl-cyclohexyl)-methyl-carbamic acid benzyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 495 g (1710.6 mmol) of (4-Methoxymethylene-cyclohexyl)-methyl-carbamic acid benzyl ester in 1.7 l THF was treated with 3.42 l of aqueous 1N HCl at RT and heated at reflux for 2 h. The reaction was cooled to RT and extracted with TBME (1.7 and 0.9 l). The organic phase was washed with aqueous 1M NaHCO3, dried (Na2SO4), filtered and evaporated to give 457.4 (97%) of crude (4-Formyl-cyclohexyl)-methyl-carbamic acid benzyl ester (trans:cis ca 70:30).

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux for 2 h
  3. extractionextracted with TBME (1.7 and 0.9 l)
  4. washThe organic phase was washed with aqueous 1M NaHCO3
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-52e68e6d168242588e042ab27a19ed37
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06858651B2

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