Methanol → Menthol

HRID 1436332Notes

Reaction equation

HRID 1436332 reaction equation
CO.C([O:5][CH:6]1[CH:11]([CH:12]([CH3:14])[CH3:13])[CH2:10][CH2:9][CH:8]([CH3:15])[CH2:7]1)=C>CC(O)C>[CH:8]1([CH3:15])[CH2:9][CH2:10][CH:11]([CH:12]([CH3:13])[CH3:14])[CH:6]([OH:5])[CH2:7]1

Participants

4

Reactant 2

HCID 887MethanolHCID 11206170HCID 11206170, compound

Product 1

HCID 1254MentholYield 73%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

The reaction was conducted in the same manner as in Example 10 except that methanol was used in stead of the solvent 2-propanol, the reaction temperature was altered to 20° C. and the reaction time was altered to 1 hour. The obtained reaction solution was analyzed by GC, to find that 27% of the menthyl vinyl ether was left with an optical purity of 58% ee. Further, the reaction solution was purified by silica gel column chromatography to obtain the reaction product menthol in a yield of 73%. Also, the kre1 value showing the selectivity of reactions at this time was 2.5.

Workup

  1. customwas altered to 20° C.
  2. customThe obtained reaction solution
  3. waitwas left with an optical purity of 58% ee
  4. customFurther, the reaction solution was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-6739a96e398143c993c7d7d5b0ce6399
Source dataset
uspto-grants-2009_11
Patent number
US07619003B2

Reaction notes

Loading…