Water → 4-Prop-2-ynylcyclohexanecarboxylic acid

HRID 254142Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 254142
OS(O)(=O)=O.[CH2:6]([CH:9]1[CH2:14][CH2:13][CH:12]([CH2:15][OH:16])[CH2:11][CH2:10]1)[C:7]#[CH:8].C([OH:20])(C)C.O>CC(C)=O.CCOCC.[O-2].[O-2].[O-2].[Cr+6]>[CH2:6]([CH:9]1[CH2:14][CH2:13][CH:12]([C:15]([OH:20])=[O:16])[CH2:11][CH2:10]1)[C:7]#[CH:8]

Komponenten

8

Edukt 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 3776IsopropanolHCID 10796940(4-Prop-2-ynylcyclohexyl)methanol

Produkt 1

HCID 107971444-Prop-2-ynylcyclohexanecarboxylic acidAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 10219390chromium (VI) trioxideKatalysatorHCID 180AcetoneLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A solution of chromium trioxide (600 mg, 6.0 mmol) in 1.5 M H2SO4 (2.6 mL, 150 mmol) was cooled to 5° C. and added to a solution of 86 (280 mg, 1.84 mmol) in acetone (15 mL). The mixture was allowed to warm to room temperature and allowed to stir overnight. Isopropanol (4 mL) was added to the green/black solution, which turned light blue after 1 hr. After adding water (15 mL), the solution was extracted with CHCl3 (6×25 mL). The organic layers were pooled and concentrated in vacuo to yield a white solid. The solid was dissolved in ether (50 mL) and extracted with 1 M NaOH (2×30 mL). The basic extracts were pooled, acidified w/10% HCl, and re-extracted with ether (3×30 mL). The ether layers were combined, dried with sodium sulfate and concentrated in vacuo to yield a white solid. The product was recrystallized from acetone/water to yield 88 (222 mg, 73%) as white needles: mp 84-85° C.; 1H NMR (CDCl3) δ 2.30-2.23 (m, 1H), 2.17-2.11 (m, 2H), 2.07-2.03 (m, 2H), 1.97-1.91 (m, 3H), 1.51-1.39 (m, 3H), 1.13-1.01 (m, 2H); 13C NMR (CDCl3) δ 182.5, 83.8, 69.6, 40.7, 37.7, 32.3, 29.6, 26.5; APCI m/z (rel intensity) 165 (M−, 100).

Aufarbeitung

  1. waitturned light blue after 1 hr
  2. extractionthe solution was extracted with CHCl3 (6×25 mL)
  3. concentrationconcentrated in vacuo
  4. customto yield a white solid
  5. extractionextracted with 1 M NaOH (2×30 mL)
  6. extractionre-extracted with ether (3×30 mL)
  7. dry with materialdried with sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customto yield a white solid
  10. customThe product was recrystallized from acetone/water

Quellen und Nachweise

ORD-Eintrag
ord-b2a85a1aa86c4a95b91f19dddc7f0a4f
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07875595B2

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