Sodium Hydroxide → HCID 67402756, compound

HRID 1514028Notes

Reaction equation

HRID 1514028 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][C@@H:8]1[CH:13]=[CH:12][CH2:11][C:10]([CH3:15])([CH3:14])[C@H:9]1[C:16](OC)=[O:17].[OH-].[Na+].[O-]S([O-])(=O)=O.[Na+].[Na+]>C1COCC1.CCOCC.CC(C)=O>[CH3:7][C@@H:8]1[CH:13]=[CH:12][CH2:11][C:10]([CH3:14])([CH3:15])[C@H:9]1[CH2:16][OH:17]

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 12082923Methyl trans-2,6,6-trimethyl-3-cyclohexene-1-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 67402756HCID 67402756, compoundYield 99%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred suspension of LiAlH4 (1.55 g, 41 mmol) in THF (50 ml) at room temperature was added dropwise a solution of methyl trans-2,6,6-trimethyl-3-cyclohexene-1-carboxylate (10.0 g, purity 98%, 54 mmol) in THF (50 ml). After two hours at room temperature, the mixture was diluted with ether (150 ml), acetone (3 ml) was added dropwise, then 1 N aqueous NaOH (8 ml) was added and the mixture was stirred at room temperature during 30 minutes. Na2SO4 was added, the solids filtered off and the filtrate concentrated. Bulb-to-bulb distillation (oven temperature 160° C./16 mbar) afforded trans-2,6,6-trimethyl-3-cyclohexene-1-methanol as a colourless liquid (8.40 g, purity >99%, yield 99%).

Workup

  1. additionwas added dropwise
  2. filtrationthe solids filtered off
  3. concentrationthe filtrate concentrated
  4. distillationBulb-to-bulb distillation (oven temperature 160° C./16 mbar)

Sources & evidence

ORD record
ord-a00ba1bddcd24630a83bbc89ff9466fe
Source dataset
uspto-grants-2012_07
Patent number
US08222198B2

Reaction notes

Loading…