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

HRID 979717Notes

Reaction equation

HRID 979717 reaction equation
[CH:1]([Mg]Br)=[CH2:2].[CH2:5]1[CH2:10][CH2:9][CH:8]([CH:11]=[O:12])[CH2:7][CH2:6]1>O1CCCC1>[CH:8]1([CH:11]([OH:12])[CH:1]=[CH2:2])[CH2:9][CH2:10][CH2:5][CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 16275CyclohexanecarboxaldehydeHCID 178418507HCID 178418507, compound

Product 1

HCID 1381961-Cyclohexylprop-2-en-1-olYield 99.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

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 three 600 ml portions of ethyl acetate. The ethyl acetate extracts were combined and washed with 1 L of saturated aqueous ammonium chloride, 1 L of saturated aqueous sodium bicarbonate, then twice with 1 L each of brine. The ethyl acetate extract was dried thoroughly over magnesium sulfate, filtered, and concentrated at room temperature via rotovap to give 31.0 g of 1-cyclohexylprop-2-enol.

Workup

  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 three 600 ml portions of ethyl acetate
  7. washwashed with 1 L of saturated aqueous ammonium chloride, 1 L of saturated aqueous sodium bicarbonate
  8. extractionThe ethyl acetate extract
  9. dry with materialwas dried thoroughly over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated at room temperature via rotovap

Sources & evidence

ORD record
ord-e7631790d5b14534949c8607ebc6827d
Source dataset
uspto-grants-1987_05
Patent number
US04668814

Reaction notes

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