Cyclohexanecarboxaldehyde → 1-Cyclohexylprop-2-en-1-ol

Temperature

0 °C

To 140 ml of dry tetrahydrofuran, degassed and flushed with nitrogen (3×) and cooled to 0° C. under nitrogen, was added 1.3M vinyl magnesium bromide (195 ml, 253.5 mmol) in tetrahydrofuran rapidly and dropwise over 5 minutes. The resulting solution was stirred for 5 minutes at 0° C. under nitrogen after which a solution of 24.0 g (223 mmol) of cyclohexylcarboxaldehyde in 40 ml of dry tetrahydrofuran was added via syringe at 0° C. The resulting mixture was stirred for 3.75 hours at 0° to 5° C. under a nitrogen atmosphere after which the reaction was quenched at 0° C. by careful addition of saturated aqueous ammonium chloride. The resulting suspension was poured into 1 L of ice cold, saturated, aqueous ammonium chloride and extracted with ethyl acetate. The ethyl acetate extracts were combined and washed with saturated aqueous ammonium chloride, saturated aqueous sodium bicarbonate, then with brine. The ethyl acetate extract was dried over magnesium sulfate, filtered, and concentrated at room temperature to give 31.0 g of 1-cyclohexyl-prop-2-enol.

1. customTo 140 ml of dry tetrahydrofuran, degassed
2. customflushed with nitrogen (3×)
3. additionwas added via syringe at 0° C
4. customwas quenched at 0° C. by careful addition of saturated aqueous ammonium chloride
5. additionThe resulting suspension was poured into 1 L of ice cold
6. extractionsaturated, aqueous ammonium chloride and extracted with ethyl acetate
7. washwashed with saturated aqueous ammonium chloride, saturated aqueous sodium bicarbonate
8. extractionThe ethyl acetate extract
9. dry with materialwas dried over magnesium sulfate
10. filtrationfiltered
11. concentrationconcentrated at room temperature

ORD record

ord-227de17d7aad4c11b862b4f2376b9a46

Source dataset

uspto-grants-1985_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04544764