HCID 14854590, compound → (1-Cyanocyclohexyl)acetic acid

HRID 974434Notes

Reaction equation

HRID 974434 reaction equation
[C:1]([C:3]1([CH:9](C(O)=O)[C:10]([OH:12])=[O:11])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1)#[N:2]>C1(C)C=CC=CC=1>[C:1]([C:3]1([CH2:9][C:10]([OH:12])=[O:11])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1)#[N:2]

Participants

3

Reactant 1

HCID 14854590HCID 14854590, compound

Product 1

HCID 11073797(1-Cyanocyclohexyl)acetic acidYield 69.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
82.5 °C

Procedure

35.5 g (1-Cyanocyclohexyl)-malonic acid are suspended in 400 mL toluene and heated, while stirring, for about one hour to 80-85° C. In the course of the decarboxylation, an almost clear solution is obtained. After filtration, the toluene is distilled off in a vacuum at 35° C. The crude product is dissolved in a saturated aqueous solution of sodium bicarbonate and stirred with ethyl acetate. After separating off the organic phase, the aqueous phase is acidified with concentrated hydrochloric acid, while cooling with ice to 5° C. The solid product which precipitates out is filtered off with suction and then washed with water. The filter cake is dissolved in ethyl acetate and the solution dried over anhydrous sodium sulphate. After filtration, the ethyl acetate is evaporated on a rotary evaporator at 35° C. The residue is dried to constant weight in a vacuum drying cabinet at 35° C. 19.6 g of the title compound are obtained (70% of theory); m.p. 102° C.

Workup

  1. temperatureheated
  2. customIn the course of the decarboxylation, an almost clear solution is obtained
  3. filtrationAfter filtration
  4. distillationthe toluene is distilled off in a vacuum at 35° C
  5. dissolutionThe crude product is dissolved in a saturated aqueous solution of sodium bicarbonate
  6. stirringstirred with ethyl acetate
  7. customAfter separating off the organic phase
  8. temperaturewhile cooling with ice to 5° C
  9. customThe solid product which precipitates out
  10. filtrationis filtered off with suction
  11. washwashed with water
  12. dissolutionThe filter cake is dissolved in ethyl acetate
  13. dry with materialthe solution dried over anhydrous sodium sulphate
  14. filtrationAfter filtration
  15. customthe ethyl acetate is evaporated on a rotary evaporator at 35° C
  16. customThe residue is dried to constant weight in a vacuum
  17. customdrying cabinet at 35° C

Sources & evidence

ORD record
ord-dfa11f63857848ae9c3d9245446b1ee6
Source dataset
uspto-grants-1991_11
Patent number
US05068413

Reaction notes

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