Water → HCID 20491276, compound

HRID 435211Notes

Reaction equation

HRID 435211 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1[C:9](=[O:20])[CH:10]([CH3:19])[CH2:11][CH:12]([CH2:14][CH2:15][CH:16]([CH3:18])[CH3:17])[CH:13]=1.O.[OH-].[Na+]>C(OCC)C>[CH3:7][C:8]1[CH:9]([OH:20])[CH:10]([CH3:19])[CH2:11][CH:12]([CH2:14][CH2:15][CH:16]([CH3:17])[CH3:18])[CH:13]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 20491275HCID 20491275, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 20491276HCID 20491276, compoundYield 84.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A suspension of lithium aluminum hydride (0.5 g, 0.013 mol) in anhydrous diethyl ether (100 mL) was stirred at 10° C. under nitrogen while 2,6-dimethyl-4-(3-methylbutyl)-2-cyclohexen-1-one (5.8 g, 0.03 mol) in anhydrous ether (10 mL) was added over a period of 30 minutes. The mixture was stirred at room temperature for 3 hours; then it was treated successively with water (0.5 mL), 15% NaOH solution (0.5 mL), and water (1.5 mL). The solution was filtered, dried and concentrated to give the crude alcohol. Short path distillation afforded 5.0 g of 2,6-dimethyl-4-(3-methylbutyl)-2-cyclohexen-1-ol, bp 90°-95° C. (1 mm), as a mixture of isomers by glc/ms (65.5%, 28%, and 5.5%). NMR (CDCl3) δ0.9-1.6 (19H, complex), 1.8 (3H, bs), 3.6 (1H, m), 5.4 (1H, m). IR (film) 3300, 1040, 1010 cm-1. MS (m/e) 196 (M+), 98, 82, 125, 107.

Workup

  1. additionwas added over a period of 30 minutes
  2. filtrationThe solution was filtered
  3. customdried
  4. concentrationconcentrated
  5. customto give the crude alcohol
  6. distillationShort path distillation

Sources & evidence

ORD record
ord-b46b856f9ba44528b613fd9e88616df8
Source dataset
uspto-grants-1983_08
Patent number
US04400545

Reaction notes

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