Hydrochloric Acid → 2-[4-(2-Hydroxycyclohexylidenemethyl)phenyl]propionic acid

HRID 1731645Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1731645
[O:1]=[C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=[CH:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([CH3:19])[C:16]([OH:18])=[O:17])=[CH:11][CH:10]=1.C([BH3-])#N.[Na+].Cl>CO>[OH:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=[CH:8][C:9]1[CH:10]=[CH:11][C:12]([CH:15]([CH3:19])[C:16]([OH:18])=[O:17])=[CH:13][CH:14]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 1296782-[4-(2-Oxocyclohexylidenemethyl)phenyl]propionic acidHCID 5003444Sodium cyanoborohydride

Produkt 1

HCID 537414562-[4-(2-Hydroxycyclohexylidenemethyl)phenyl]propionic acidAusbeute 17,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

2.0 g of (+)-2-[4-(2-oxocyclohexylidenemethyl)phenyl]propionic acid and 0.6 g of sodium cyanoborohydride were dissolved in 50 ml of methanol. The pH of the mixture was adjusted to a value of 3 with 6N hydrochloric acid, whilst ice-cooling. The mixture was then stirred, with heating, for 40 minutes. Ice-water was added to the reaction mixture, which was then extracted with diethyl ether. The extract was washed with water and dried over anhydrous sodium sulphate, and the solvent was distilled off, to give 350 mg of (±)-2-[4-(2-hydroxycyclohexylidenemethyl)phenyl]propionic acid as crystals [compound of formula (VI)]. These crystals were dissolved in 10 ml of ethyl acetate, 50 mg of palladium chloride were added, and the mixture was subjected to catalytic reduction whilst bubbling hydrogen through the mixture. After the theoretical amount of hydrogen had been absorbed, the catalyst was removed by filtration and the solvent was distilled off, to give 330 mg of a mixture of the cis- and trans-isomers. This mixture was treated in the same manner as in Example 1, affording crystals of the cis- and trans-isomers of the title compound, having the same properties as the product of Example 1.

Aufarbeitung

  1. temperaturecooling
  2. temperaturewith heating, for 40 minutes
  3. extractionwas then extracted with diethyl ether
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous sodium sulphate
  6. distillationthe solvent was distilled off

Quellen und Nachweise

ORD-Eintrag
ord-1f715d49d3494f7591db4fb21846876f
Quelldatensatz
uspto-grants-1986_11
Patentnummer
US04622421

Notizen zur Reaktion

Wird geladen…