Carbon Dioxide → HCID 11205957, compound

HRID 247105Notes

Reaction equation

HRID 247105 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=1[CH:4]=[C:5]([C:9]#[N:10])C(O)=O.C(=O)=O>[Cu]>[Cl:1][C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=1/[CH:4]=[CH:5]\[C:9]#[N:10]

Participants

4

Reactant 2

HCID 280Carbon DioxideHCID 543182723-(2-Chlorophenyl)-2-cyano-2-propenoic acid

Product 1

HCID 11205957HCID 11205957, compound

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Procedure

o-Chlorobenzalcyanoacetic acid (40 g; 0.193 m) was intimately mixed with copper powder (3 g) and cuprous oxide (1 g) and heated in vacuo at a temperature of 240° C. with vigorous evolution of carbon dioxide. The distillate was a pale yellow oil which was shown to contain 71% cis-nitrile by NMR assay. Fractional distillation of the mixture was carried out collecting early fractions containing pure cis-isomer, b.p. 90°-92° C. at 1.2 mm/Hg.

Workup

  1. distillationFractional distillation of the mixture
  2. customwas carried out collecting early fractions
  3. additioncontaining pure cis-isomer, b.p. 90°-92° C. at 1.2 mm/Hg

Sources & evidence

ORD record
ord-cd302b06f7a84614b16bb1dadd6f08f3
Source dataset
uspto-grants-1987_11
Patent number
US04705807

Reaction notes

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