Reacción #1755469

Ecuación de reacción

water

H2SO4

86

(4-Prop-2-ynyl-cyclohexyl)-methanol

Isopropanol

→

88

Rendimiento 73.0%

4-prop-2-ynyl-cyclohexanecarboxylic acid

Rendimiento 73.0%

Disolventes

ether

acetone

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.WAITturned light blue after 1 hr
2. 2
   Extracciónthe solution was extracted with CHCl3 (6×25 mL)
3. 3
   Concentraciónconcentrated in vacuo
4. 4
   Otroto yield a white solid
5. 5
   Extracciónextracted with 1 M NaOH (2×30 mL)
6. 6
   Extracciónre-extracted with ether (3×30 mL)
7. 7
   Secadodried with sodium sulfate
8. 8
   Concentraciónconcentrated in vacuo
9. 9
   Otroto yield a white solid
10. 10
    OtroThe product was recrystallized from acetone/water

Procedimiento

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).

Fuente