Isopropyl Stearate → (R)-(-)-2-DECANOL

HRID 1939754Notes

Reaction equation

[C:1]([O:20]C(C)C)(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]CCCCCCCCC.[CH2:24](O)CCCCCCCCCCCCCCCCC>>[CH3:24][C@@H:1]([OH:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

Reactant 2

HCID 8162Isopropyl Stearate

HCID 8221Stearyl Alcohol

Product 1

HCID 2737541(R)-(-)-2-DECANOLYield 72%

Procedure

To the distillation residue, i.e., a mixture of (R)-(-)-2-decanol stearic acid ester and unreacted isopropyl stearate, were added 90 g of stearyl alcohol and 3 g Lipase PL. After regulating the particle size of the enzyme by ultrasonication in the same manner as described above, interesterification was carried out at 85° C. for 48 hours. The reaction mixture was subjected to simple distillation at 90° C. and 3 mmHg to recover highly pure free (R)-(-)-2-decanol (yield: 72%; chemical purity: 99.6%; optical purity: 84% ee).

Workup

customby ultrasonication in the same manner
distillationThe reaction mixture was subjected to simple distillation at 90° C.

Sources & evidence

ORD record: ord-80983c2c0007473c8b21211d5c49134f
Source dataset: uspto-grants-1997_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05696299

Reaction notes

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