Hydrochloric Acid → (-)-Menthol

HRID 541175Notes

Reaction equation

HRID 541175 reaction equation
[C:1]1(CCC(O)C)C=CC=CC=1.[CH2:12]1[CH:17]2[CH:18]3[NH+]([O-])[CH:15]([CH2:16]2)[CH2:14][CH:13]1[CH2:19]3.[Br-].[K+].Cl.OO.[C:27](=[O:30])([O-])[O-].[Na+].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl>[CH3:12][C@H:17]1[CH2:16][C@@H:27]([OH:30])[C@H:13]([CH:14]([CH3:15])[CH3:1])[CH2:19][CH2:18]1

Participants

9

Reactant 7

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 10340Sodium CarbonateHCID 24477Sodium ThiosulfateHCID 613024-Phenyl-2-butanolHCID 253877Potassium BromideHCID 1015366402-Oxido-2-azoniatricyclo[3.3.1.03,7]nonane

Product 1

HCID 16666(-)-Menthol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-phenylbutan-2-ol (100.1 mg, 0.666 mmol), Nor-AZADO (0.92 mg, 6.66 μmol), potassium bromide (39.7 mg, 0.333 mmol) and hydrochloric acid (11.1 μl, 0.133 mmol) in dichloromethane (0.67 ml) was added with 30% aqueous hydrogen peroxide (102.1 μl, 1.000 mmol), and the mixture was stirred at room temperature for 4 hours. The reaction mixture was added with saturated aqueous sodium carbonate (2 ml) and saturated aqueous sodium thiosulfate (2 ml), and the mixture was stirred at room temperature for 2 hours, and then extracted with dichloromethane. The organic layer was dried over sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the objective compound (95.3 mg; yield, 96.5%). The spectrum data were found to be the same as those obtained in Example 5, (b).

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hours
  2. extractionextracted with dichloromethane
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography
  6. customto obtain
  7. customthe objective compound (95.3 mg; yield, 96.5%)

Sources & evidence

ORD record
ord-46350c46f0f2400d91ae0b7fa9f686fe
Source dataset
uspto-grants-2014_10
Patent number
US08871981B2

Reaction notes

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