Hydrochloric Acid → (1r,2s,4r)-2-Hydroxy-4-methylcyclohexanecarboxylic acid

HRID 73197Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 73197
[OH-].[Na+].BrBr.O(Br)[Na].[OH:8][C@H:9]1[CH2:14][C@H:13]([CH3:15])[CH2:12][CH2:11][C@H:10]1[C:16](=[O:18])C.[O-:19]S([O-])=O.[Na+].[Na+].Cl>O.O1CCOCC1>[OH:8][C@H:9]1[CH2:14][C@H:13]([CH3:15])[CH2:12][CH2:11][C@H:10]1[C:16]([OH:18])=[O:19]

Komponenten

9

Edukt 6

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24408BromineHCID 24437Sodium SulfiteHCID 597523071-(2-Hydroxy-4-methylcyclohexyl)ethanone, (1R,2S,4R)-HCID 178507097sodium hypobromite2×

Produkt 1

HCID 45084907(1r,2s,4r)-2-Hydroxy-4-methylcyclohexanecarboxylic acidAusbeute 94,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 312751,4-DioxaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
12.5 °C

Versuchsvorschrift

To a ice-cold solution of NaOH (4.8 g, 119.2 mmol) in water (40 mL) and 1,4-dioxane (30 mL) was added bromine (1.5 mL, 29.57 mmol). To the resultant NaOBr yellow solution was added drop wise a solution (1R,2S,4R)-1-(2-Hydroxy-4-methyl-cyclohexyl)-ethanone (1.4 g, 8.962 mmol) in dioxane (130 mL) and water (35 mL). The resulting solution was stirred for 3 h at 10-15° C. The excess NaOBr solution was decomposed by adding a solution of Na2SO3 (1.1 g in 11 mL water), acidified with 10% HCl, extracted with DCM. The combined organic extract was washed with brine, dried and concentrated to give (1R,2S,4R)-2-hydroxy-4-methyl-cyclohexanecarboxylic acid (1.30 g, 92%). NMR 1H (CDCl3, 400 MHz): 4.34 ppm (s, 1H); 2.43-2.39 ppm (m, 1H); 1.96-1.76 ppm (m, 5H); 1.14-1.08 ppm (m, 1H); 1.02-0.93 ppm (m, 1H); 0.90 ppm (d, 3H).

Aufarbeitung

  1. extractionextracted with DCM
  2. extractionThe combined organic extract
  3. washwas washed with brine
  4. customdried
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-a0fc90ad45174637b5b33962bf72efe0
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829030B2

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