Diisobutylaluminum hydride → 2-Cyclohexylacetaldehyde

HRID 2236183Notes

Reaction equation

HRID 2236183 reaction equation
[CH:1]1([CH2:7][C:8](OC)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CC(C[AlH]CC(C)C)C.O.O.O.O.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>CCOCC.O>[CH:1]1([CH2:7][CH:8]=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 14487Diisobutylaluminum hydrideHCID 139743Cyclohexaneacetic acid, methyl esterHCID 2724148Sodium potassium tartrate tetrahydrate

Product 1

HCID 3166272-CyclohexylacetaldehydeYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of methyl cyclohexylacetate (1.56 g, 10 mmol) in 25 mL anhydrous ether was stirred at −78° C. under argon. DIBAL (1M in hexane, 11 mL, 11 mmol) was added dropwise over 45 minutes and the reaction mixture was stirred for an additional 1 hour. A solution of potassium sodium tartrate tetrahydrate (6 g, 12.2 mmol) in 25 mL water was added and the mixture stirred at room temperature overnight. After dilution with ether, the organic layer was washed with 0.5 N HCl, saturated sodium bicarbonate and saturated sodium chloride, dried over sodium sulfate, filtered and concentrated to give cyclohexyl-acetaldehyde (1.17 g, 93%).

Workup

  1. stirringthe mixture stirred at room temperature overnight
  2. washAfter dilution with ether, the organic layer was washed with 0.5 N HCl, saturated sodium bicarbonate and saturated sodium chloride
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2c568d5a5e654647bb7d3c10ecc2cda0
Source dataset
uspto-grants-2010_05
Patent number
US07714126B2

Reaction notes

Loading…