Water → Cycloheptanemethanol

HRID 1631887Notes

Reaction equation

HRID 1631887 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH:7]1([C:14](O)=[O:15])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.O.[OH-].[Na+]>CCOCC>[CH:7]1([CH2:14][OH:15])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 15091Cycloheptanecarboxylic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 78193CycloheptanemethanolYield 83.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

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.

Workup

  1. temperaturecooled with an ice bath
  2. stirringThe reaction was stirred vigorously for 5 minutes
  3. customthe resultant white precipitate was removed by filtration
  4. washwashed with copious Et2O
  5. customThe combined filtrate and washings were evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-26c5f5dc293c4bccb173b3590dd5b4f1
Source dataset
uspto-grants-2014_07
Patent number
US08791303B2

Reaction notes

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