Linoleoyl chloride → (7Z,10Z)-hexadeca-7,10-dienoic anhydride

HRID 1788309Notes

Reaction equation

HRID 1788309 reaction equation
[C:1](Cl)(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16]CC.N[CH:22]([CH3:26])[C:23]([O-:25])=[O:24].[NH4+]>>[C:23]([O:25][C:1](=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]/[CH:7]=[CH:8]\[CH2:9]/[CH:10]=[CH:11]\[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])(=[O:24])[CH2:22][CH2:26][CH2:13][CH2:12][CH2:11]/[CH:10]=[CH:9]\[CH2:8]/[CH:7]=[CH:6]\[CH2:5][CH2:4][CH2:3][CH2:2][CH3:1]

Participants

3

Reactant 2

HCID 9817754Linoleoyl chloride2×HCID 86624725HCID 86624725, compound

Product 1

HCID 86624724(7Z,10Z)-hexadeca-7,10-dienoic anhydride

Procedure

Finally, in a dry 2-necked, round bottomed flask, fixed with a separatory funnel, containing 17.93 g (60 mmol) of the prepared (9Z,12Z)-octadeca-9,12-dienoyl chloride, and side arm water condenser fixed with a dry receiving flask, is placed 7.64 g (72 mmol) of ammonium 2-aminopropanoate. The round bottomed flask is placed in an ice bath and the (9Z,12Z)-octadeca-9,12-dienoyl chloride is added drop wise. After addition is completed the mixture is shaken and the ice bath is replaced by a heating mantle. The flask is then heated until no more solution is dropping into the receiving flask. This crude distillate is then further fractionally distilled to yield 2-aminopropanoic (7Z,10Z)-hexadeca-7,10-dienoic anhydride.

Workup

  1. customFinally, in a dry 2-necked, round bottomed flask, fixed with a separatory funnel
  2. customThe round bottomed flask is placed in an ice bath
  3. additionAfter addition
  4. temperatureThe flask is then heated until no more solution
  5. distillationThis crude distillate is then further fractionally distilled

Sources & evidence

ORD record
ord-a4c3049184d5482a8a34391cdcb4880c
Source dataset
uspto-grants-2009_03
Patent number
US07511162B2

Reaction notes

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