Water → Cycloheptanemethanol

Participants

Reaction Steps

To an oven-dried, three-necked flask under an N2 atmosphere was added LiAlH4 (4.0 g, 0.11 mol) followed by anhydrous Et2O (100 ml). To the stirred suspension was added dropwise over 1 hour a solution of cycloheptane carboxylic acid (5.0 g, 0.035 mol) in anhydrous Et2O (50 ml). The reaction was stirred at room temperature for 2 hours and then cooled with an ice bath. H2O (4 ml) was added cautiously dropwise over 20 minutes, followed by cautious dropwise addition of NaOH (4 ml of a 15% aqueous solution) and then dropwise addition of further H2O (12 ml). The reaction was stirred vigorously for 5 minutes and the resultant white precipitate was removed by filtration and washed with copious Et2O. The combined filtrate and washings were evaporated to dryness under reduced pressure to yield the desired compound (3.74 g) as a colourless oil with no need for further purification.

Provenance & Evidence