Malonic Acid → HCID 54382735, compound

HRID 2215877Notes

Reaction equation

HRID 2215877 reaction equation
[CH3:1][CH:2]([CH3:10])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]C=O.[C:11](O)(=O)[CH2:12][C:13]([OH:15])=[O:14].S(=O)(=O)(O)O>N1C=CC=CC=1>[CH3:1][CH:2]([CH3:10])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH:11]=[CH:12][C:13]([OH:15])=[O:14]

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 1118Sulfuric AcidHCID 169665Isononanal

Product 1

HCID 54382735HCID 54382735, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a similar reaction as in 1 above, 100 ml toluene, sodium (39.5 g, 1.72 mole), 7-methyl-octanoate (52 g, 0.29 mole), and 260 ml anhydrous methanol reacted to yield 7-methyl-1-octanol (44.3 g, yield rate 85%); 7-methyl-1-octanol (44.3 g, 0.31 mole) reacted with chloro-chromic pyridine (100 g, 0.465 mole) to yield 7-methyl-octanaldehyde (31 g, yield rate 70%); and finally, 7-methyl-octanaldehyde (20 g, 0.14 mole), malonic acid (15 g, 0.14 mole), and 15 ml pyridine were added together and refluxed with heating for 3 hours. After cooling down 15 ml 30% sulfuric 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 122° C./1.5 mmHg fraction was collected as 9-methyl-2-decenoic acid (16 g, yield rate 80%).

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 122° C./1.5 mmHg fraction
  7. customwas collected as 9-methyl-2-decenoic acid (16 g, yield rate 80%)

Sources & evidence

ORD record
ord-7f306ac1fc554c319865aa322350a19f
Source dataset
uspto-grants-2006_09
Patent number
US07109364B2

Reaction notes

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