Malonic Acid → 15-Methylhexadec-2-enoic acid

HRID 2215875Notes

Reaction equation

HRID 2215875 reaction equation
[CH3:1][CH:2]([CH3:16])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]C=O.[C:17](O)(=O)[CH2:18][C:19]([OH:21])=[O:20].N1C=CC=CC=1>>[CH3:1][CH:2]([CH3:16])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:17]=[CH:18][C:19]([OH:21])=[O:20]

Participants

4

Reactant 3

HCID 867Malonic AcidHCID 1049PyridineHCID 1108550713-methyltetradecanal

Product 1

HCID 5427800115-Methylhexadec-2-enoic acid

Procedure

13-methyl-tetradecanaldehyde (56.5 g, 0.25 mole), malonic acid (26.5 g, 0.51 mole), and pyridine (30.8 ml, 0.374 mole) were added to a flask and refluxed with heating for 3 hours. After cooling down 30% sulfuic acid was added and the reaction mixture was stirred for 3 hours under ice bath and then extracted by diethyl ether. Diethyl ether was removed by evaporation and product was subject to vacuum fractional distillation and 170–172° C./1.0 mmHg fraction was collected as 15-methyl-2-hexadecenoic acid (50.9 g, yield rate 76%).

Workup

  1. temperaturerefluxed
  2. temperaturewith heating for 3 hours
  3. additionwas added
  4. extractionextracted by diethyl ether
  5. customDiethyl ether was removed by evaporation and product
  6. distillationwas subject to vacuum fractional distillation and 170–172° C./1.0 mmHg fraction
  7. customwas collected as 15-methyl-2-hexadecenoic acid (50.9 g, yield rate 76%)

Sources & evidence

ORD record
ord-295a3875713942908477f0183817fe89
Source dataset
uspto-grants-2006_09
Patent number
US07109364B2

Reaction notes

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