HCID 11206170, compound → Menthol

HRID 1436333Notes

Reaction equation

HRID 1436333 reaction equation
C([O:3][CH:4]1[CH:9]([CH:10]([CH3:12])[CH3:11])[CH2:8][CH2:7][CH:6]([CH3:13])[CH2:5]1)=C>CO>[CH:6]1([CH3:13])[CH2:7][CH2:8][CH:9]([CH:10]([CH3:11])[CH3:12])[CH:4]([OH:3])[CH2:5]1

Participants

3

Reactant 1

HCID 11206170HCID 11206170, compound

Product 1

HCID 1254MentholYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The reaction was conducted in the same manner as in Example 10 except that methanol was used instead of the solvent and the reaction time was altered to 2 hours. The obtained reaction solution was analyzed by GC, to find that 12% of the menthyl vinyl ether was left with an optical purity of 76% ee. Further, the reaction solution was purified by silica gel column chromatography to obtain the reaction product menthol in a yield of 88%. Also, the kre1 value showing the selectivity of reactions at this time was 2.3.

Workup

  1. customThe obtained reaction solution
  2. waitwas left with an optical purity of 76% ee
  3. customFurther, the reaction solution was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-661489de984841c8a2b6069b6ea33ad7
Source dataset
uspto-grants-2009_11
Patent number
US07619003B2

Reaction notes

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