Methanesulfonic Acid → Decyl cyanoacetate

HRID 650296Notes

Reaction equation

[C:1]([CH2:3][C:4]([OH:6])=[O:5])#[N:2].[CH2:7](O)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].CS(O)(=O)=O>>[C:1]([CH2:3][C:4]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[O:5])#[N:2]

Participants

Reactant 3

HCID 6395Methanesulfonic Acid

HCID 81741-Decanol

HCID 9740Cyanoacetic acid

Product 1

HCID 87237Decyl cyanoacetate

Conditions

Temperature: 130 °C

Procedure

Cyanoacetic acid (85.5 g; 1.0 mol), decyl alcohol (206 g; 1.30 mol) and methanesulfonic acid (0.47 g; 0.005 mol) were introduced into a 500 ml flask under a nitrogen atmosphere. The mixture was warmed slowly to a maximum temperature of 130° C., while gradually reducing the pressure to about 10 mm of Hg. Water was continuously removed from the distillates (bp 60-65° C./50 mm of Hg) and the organic layer of decyl alcohol was returned to the flask until the reaction was complete. After distilling off the unreacted decyl alcohol, the decyl cyanoacetate (bp 143° C./1 mm of Hg) was isolated as a clear liquid. The yield was 219 g (97% of theoretical) with a purity of >99% (GC assay).

Workup

customWater was continuously removed from the distillates (bp 60-65° C./50 mm of Hg)
distillationAfter distilling off the unreacted decyl alcohol

Sources & evidence

ORD record: ord-eca6aa8a05244f108985221a026d1d82
Source dataset: uspto-grants-2001_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06271410B1

Reaction notes

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