Citronellal → (-)-Isopulegol

HRID 607342

Reaction equation

HRID 607342 reaction equation
[CH3:1][C:2](=[CH:4][CH2:5][CH2:6][CH:7]([CH2:9][CH:10]=[O:11])[CH3:8])[CH3:3].[OH-].[Na+]>CC1C=CC=C(CC2C=CC=CC=2)C=1CC1C=CC=CC=1>[CH3:8][C@H:7]1[CH2:9][C@@H:10]([OH:11])[C@H:4]([C:2]([CH3:3])=[CH2:1])[CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 7794CitronellalHCID 14798Sodium Hydroxide

Product 1

HCID 170833(-)-Isopulegol

Reagents, catalysts & solvents 1

HCID 3034397Methylbis(phenylmethyl)benzeneSolvent

Procedure

The aluminium siloxide (Ia) or (Ib) was prepared analogously to Example 4 in 5 ml Marlotherm S® (isomer mixture of isomeric dibenzyltoluenes). 200 mmol citronellal were then added at room temperature to a solution containing 2 mmol of freshly prepared aluminium siloxide over a period of 15 min. When the metering in had ended, the reaction mixture was stirred at room temperature for a further 2 h and the reaction was then interrupted by addition of 50 ml 15% strength sodium hydroxide solution. After washing neutral and distilling off the solvent, the reaction product B2 was obtained as a colourless oil, yield: 14.8 g.

Workup

  1. washAfter washing neutral
  2. distillationdistilling off the solvent

Sources & evidence

ORD record
ord-ebaa780403244f60a506743c693edb23
Source dataset
uspto-grants-2011_03
Patent number
US07915457B2

Linked notes

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