Cetyl Alcohol → Hexadecyl cis-10-tetradecenoate

HRID 2410629Notes

Reaction equation

HRID 2410629 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][CH2:9]/[CH:10]=[CH:11]\[CH2:12][CH2:13][CH3:14]

Participants

3

Reactant 1

HCID 2682Cetyl Alcohol

Product 1

HCID 46700773Hexadecyl cis-10-tetradecenoateYield 80%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

cis-10-Myristoleate, 7 (3.35 g, 0.014 mol) was enzymatically transesterified with cetyl alcohol (4.07 g, 0.0168 mol) in the presence of Novozyme 435 (0.745 g, 10 wt % of the total substrate), at 65 degree. C for 8 hr. The reaction was monitored by TLC and after completion of 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-10-tetradecenoate, 8 (5.55 g, 0.0123) in 80% yield with 90% purity by GC. The structure of hexadecyl cis-10-tetradecenoate, 8 was confirmed by 1H NMR, IR, and GC-MS.

Workup

  1. customat 65 degree
  2. additionwas added
  3. customthe lipase was separated by filtration
  4. customthe solvent was evaporated
  5. customto get the crude product
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-deca41be93d144a6b20eb59af18c29ee
Source dataset
uspto-grants-2014_08
Patent number
US08816109B2

Reaction notes

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