Cyclohexanebutanoic acid → Cyclohexanebutanol

HRID 1110842Notes

Reaction equation

HRID 1110842 reaction equation
[CH2:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8][CH2:9][C:10](O)=[O:11])[CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH2:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8][CH2:9][CH2:10][OH:11])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 75200Cyclohexanebutanoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 78182Cyclohexanebutanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-cyclohexanebutyric acid in 15 ml of THF at 0° is added 15 ml of a 1M solution of lithium aluminum hydride in THF. After the gas evolution ceases, the reaction is allowed to warm to room temperature. After stirring for six hours the reaction is cooled to 0° and quenched by carefully adding 2N HCl. The mixture is diluted with ether, and the layers are separated. The organic layer is then washed with saturated aqueous brine, and then dried (sodium sulfate/magnesium sulfate). Evaporation of the solvents in vacuo gives 4-cyclohexanebutanol as a clear oil. This oil is then dissolved in 20 ml of dry methylene chloride containing 3.5 ml of triethylamine and 2.85 g of p-toluenesulfonyl chloride. After stirring for 22 hours the reaction is quenched with water and stirred vigorously. The mixture is basified with 2N sodium hydroxide and extracted twice with methylene chloride. After drying (sodium sulfate), the solvents are evaporated in vacuo. Flash chromatography (50% methylene chloride/hexane) gives 4-cyclohexylbutyl 4-methylbenzenesulfonate as a clear oil.

Workup

  1. temperatureis cooled to 0°
  2. customquenched
  3. additionby carefully adding 2N HCl
  4. additionThe mixture is diluted with ether
  5. customthe layers are separated
  6. washThe organic layer is then washed with saturated aqueous brine
  7. dry with materialdried (sodium sulfate/magnesium sulfate)
  8. customEvaporation of the solvents in vacuo

Sources & evidence

ORD record
ord-3c3f2dc0b71f451f809586f968d15a3d
Source dataset
uspto-grants-1990_12
Patent number
US04977144

Reaction notes

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