Cetyl Alcohol → Cetyl Myristoleate

HRID 2410627Notes

Reaction equation

HRID 2410627 reaction equation
[CH2:1]([OH:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]>CCCCCC>[C:1]([O:17][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH3:14]

Participants

3

Reactant 1

HCID 2682Cetyl Alcohol

Product 1

HCID 6443825Cetyl MyristoleateYield 90%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

cis-9-Myristoleate, 3 (4.2 g, 0.0175 mol) was enzymatically transesterified with cetyl alcohol (5.08 g, 0.021 mol) in the presence of Novozyme 435 (0.930 g, 10 wt % of the total substrate) at 68° C. for 8 hr. The reaction was monitored by TLC and after completion of the reaction, hexane (50 ml) was added and the lipase was separated by filtration and the solvent was evaporated to get the crude product and was purified by column chromatography to obtain hexadecyl cis-9-tetradecenoate, 4 (7.48 g, 0.0166 mol) in 90% yield with 90% purity by GC. The structure of hexadecyl cis-9-tetradecenoate, 4 was confirmed by 1H NMR, IR, and GC-MS.

Workup

  1. customat 68° C.
  2. customfor 8 hr
  3. additionwas added
  4. customthe lipase was separated by filtration
  5. customthe solvent was evaporated
  6. customto get the crude product
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-e453da16b0694da4add7501e0fe3f6a9
Source dataset
uspto-grants-2014_08
Patent number
US08816109B2

Reaction notes

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