(-)-Isopulegol → (-)-Menthol

HRID 2423380Notes

Reaction equation

[CH3:1][C@H:2]1[CH2:7][C@@H:6]([OH:8])[C@H:5]([C:9]([CH3:11])=[CH2:10])[CH2:4][CH2:3]1.[H][H]>>[CH3:1][C@H:2]1[CH2:7][C@@H:6]([OH:8])[C@H:5]([CH:9]([CH3:11])[CH3:10])[CH2:4][CH2:3]1

Participants

Reactant 2

HCID 170833(-)-Isopulegol

HCID 178418361HCID 178418361, compound

Product 1

HCID 16666(-)-Menthol

Conditions

Temperature: 80 °C

Procedure

Example 1 was repeated using L-isopulegol with a purity of 99.9% by weight and 99.8% ee, which was introduced at a rate of 12.6 g/h (total amount 303 g) into the reactor at a hydrogen pressure of 40 bar. The main reactor (MR) was heated to 80° C., the postreactor to 75° C. L-menthol (99.8% ee) was obtained in an amount of 306 g corresponding to a rate of 12.8 g/h. The chemical purity of the L-menthol output is compiled in Table 2.

Workup

customto 75° C

Sources & evidence

ORD record: ord-e927ec18400f4fb68541b3cfdd6578e9
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960593B2

Reaction notes

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