Water → (1-Methylcyclohexyl)methanol

HRID 1009183Notes

Reaction equation

HRID 1009183 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][C:8]1([C:14](O)=[O:15])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.[OH-].[Na+].O>C1COCC1>[CH3:7][C:8]1([CH2:14][OH:15])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 707441-Methylcyclohexanecarboxylic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 1501840(1-Methylcyclohexyl)methanolYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
4 °C

Procedure

To a stirring solution of LiAlH4 (20 mmol) in anhydrous THF (10 mL) at 4° C. was added 1-methyl-cyclohexanecarboxylic acid (i, 7.0 mmol) in 50 mL of THF dropwise over a period of 1 hour. The solution was stirred at refluxing temperature under N2 for 6 hours. The solution was cooled to 4° C. by ice bath, and 1 mL of 1 N NaOH (1 mL) followed by H2O (2 mL) was slowly added to the solution to quench the reaction. The solution was stirred at 23° C. for 1 hour and then filtered to remove solid material. The solution was concentrated. Purification by flash silica gel chromatography (ethyl acetate/hexanes, 1:2) gave the product, (1-methyl-cyclohexyl)-methanol (ii), in 82% yield.

Workup

  1. temperatureat refluxing temperature under N2 for 6 hours
  2. additionwas slowly added to the solution
  3. customto quench
  4. customthe reaction
  5. stirringThe solution was stirred at 23° C. for 1 hour
  6. filtrationfiltered
  7. customto remove solid material
  8. concentrationThe solution was concentrated
  9. customPurification by flash silica gel chromatography (ethyl acetate/hexanes, 1:2)

Sources & evidence

ORD record
ord-d46e243d15404b39811532d7f857cc48
Source dataset
uspto-grants-2011_07
Patent number
US07973062B2

Reaction notes

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