Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → Ethyl 9-cyanonon-2-enoate

HRID 1678924Notes

Reaction equation

HRID 1678924 reaction equation
[C:1]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=O)#[N:2].C1(P(=[CH:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1C=CC=CC=1>[CH2:34]([O:33][C:31](=[O:32])[CH:30]=[CH:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][C:1]#[N:2])[CH3:35]

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 109205897-CYANOHEPTANAL

Product 1

HCID 54099068Ethyl 9-cyanonon-2-enoate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The starting material is prepared as follows: The mixture of 14 g of 7-cyanoheptanal, 38 g of ethyl triphenylphosphoranylidene-acetate and 100 ml of benzene is refluxed for 15 hours and evaporated. The residue is triturated with diethyl ether, filtered and the filtrate evaporated. The residue is allowed to stand overnight in the refrigerator, triturated with the minimum amount of diethyl ether, the suspension filtered, the filtrate evaporated, the residue distilled and the fraction boiling at 130°-138°/0.1 mm Hg collected, to yield the 9-cyano-2-nonenoic acid ethyl ester of the formula

Workup

  1. customThe starting material is prepared
  2. temperatureis refluxed for 15 hours
  3. customevaporated
  4. customThe residue is triturated with diethyl ether
  5. filtrationfiltered
  6. customthe filtrate evaporated
  7. customtriturated with the minimum amount of diethyl ether
  8. filtrationthe suspension filtered
  9. customthe filtrate evaporated
  10. distillationthe residue distilled
  11. customthe fraction boiling at 130°-138°/0.1 mm Hg collected

Sources & evidence

ORD record
ord-d062197b0b464e60b2d779518828a39f
Source dataset
uspto-grants-1978_03
Patent number
US04077979

Reaction notes

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