Adipic Acid → HCID 12349930, compound

HRID 2417761Notes

Reaction equation

HRID 2417761 reaction equation
C(O)(=O)CCCCC(O)=O.C(OC)(=O)[CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17].C(#N)CCCC[C:28]#[N:29]>CO>[C:28]([CH:15]([CH2:14][CH2:13][CH3:12])[C:16]([O:18][CH3:19])=[O:17])#[N:29]

Participants

5

Reactant 3

HCID 196Adipic AcidHCID 8128AdiponitrileHCID 12329Dimethyladipate

Product 1

HCID 12349930HCID 12349930, compoundYield 203.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
230 °C

Procedure

Into a 1-liter, stainless autoclave were introduced 301.2 g of Solution A, 39.4 g (0.270 mole) of adipic acid, 51.8 g (0.298 mole) of dimethyl adipate and 29.2 g (0.270 mole) of adiponitrile. The content of the autoclave was stirred at 230° C. for 2.5 hours. After cooling the reaction mixture, 160.0 g of methanol was added and the resulting mixture was stirred at 200° C. for 2 hours. Then, the liquid reaction mixture was distilled under reduced pressure to obtain 77.5 g (0.550 mole) of methyl cyanovalerate. The yield thereof corresponded to 203.7% based on the adipic acid charged.

Workup

  1. additionwas added
  2. stirringthe resulting mixture was stirred at 200° C. for 2 hours
  3. customThen, the liquid reaction mixture
  4. distillationwas distilled under reduced pressure

Sources & evidence

ORD record
ord-726b9b98cf6a4f1cac3cb13ea2f53b7f
Source dataset
uspto-grants-1984_09
Patent number
US04470928

Reaction notes

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