Water → Cyclohexanol, 3,5-dimethyl-4-(3-methyl-2-buten-1-yl)-

HRID 2286142Notes

Reaction equation

HRID 2286142 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][CH:8]1[CH:13]([CH2:14][CH:15]=[C:16]([CH3:18])[CH3:17])[CH:12]([CH3:19])[CH2:11][C:10](=[O:20])[CH2:9]1.O.[OH-].[Na+]>C(OCC)C>[CH3:19][CH:12]1[CH:13]([CH2:14][CH:15]=[C:16]([CH3:18])[CH3:17])[CH:8]([CH3:7])[CH2:9][CH:10]([OH:20])[CH2:11]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 20469263Cyclohexanone, 3,5-dimethyl-4-(3-methyl-2-buten-1-yl)-HCID 21226445Aluminium lithium hydride

Product 1

HCID 20469306Cyclohexanol, 3,5-dimethyl-4-(3-methyl-2-buten-1-yl)-Yield 90.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A suspension of lithium aluminum hydride (0.68 g, 0.018 mol) in anhydrous diethyl ether (50 mL) was stirred under nitrogen at 10° C. while 3,5-dimethyl-4-(3-methyl-2-butenyl) cyclohexanone (6.8 g, 0.035 mol) in anhydrous ether (15 mL) was added over a period of 30 minutes. The mixture was stirred at room temperature for 2 hours; then it was treated successively with H2O (0.7 mL), 15% NaOH (0.7 mL), and H2O (2.1 mL). The solution was filtered, dried (NaSO4), and concentrated to give the crude alcohol as a colorless oil. Kugelrohr distillation afforded 6.2 g of 3,5-dimethyl-4-(3-methyl-2-butenyl) cyclohexanol, bp 130° C./0.3 mm.

Workup

  1. additionwas added over a period of 30 minutes
  2. filtrationThe solution was filtered
  3. dry with materialdried (NaSO4)
  4. concentrationconcentrated
  5. customto give the crude alcohol as a colorless oil
  6. distillationKugelrohr distillation

Sources & evidence

ORD record
ord-80cbbfa97ee64b04a634ca55906d45b2
Source dataset
uspto-grants-1982_04
Patent number
US04326996

Reaction notes

Loading…