Hydrochloric Acid → Ethyl 3-methyl-1-cyanocyclohexanecarboxylate

HRID 231458Notes

Reaction equation

HRID 231458 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH:4]([C:8]#[N:9])[CH2:3]1.C([N-]C(C)C)(C)C.[Li+].[C:18](=O)([O:22]CC)[O:19][CH2:20][CH3:21].Cl>C1COCC1>[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][C:4]([C:8]#[N:9])([C:18]([O:19][CH2:20][CH3:21])=[O:22])[CH2:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7766Diethyl CarbonateHCID 2724682Lithium diisopropylamideHCID 198007403-Methylcyclohexane-1-carbonitrile

Product 1

HCID 20032648Ethyl 3-methyl-1-cyanocyclohexanecarboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 17 g of 3-methylcyclohexanecarbonitrile in 140 ml of THF has added to it, at -78°, a lithium diisopropylamide solution (prepared from 140 ml of THF, 16 g of diisopropylamine and 100 ml of 1.6-molar butyllithium solution in hexane), followed, after 2 hours, by 25 g of diethyl carbonate, and stirring is continued for one hour. After heating to room temperature and pouring onto 300 ml of ice-water the mixture is neutralized with dilute hydrochloric acid. Customary working up and distillation gives ethyl 3-methyl-1-cyanocyclohexanecarboxylate.

Workup

  1. distillationdistillation

Sources & evidence

ORD record
ord-4edf001ca10347a088854b8840660cf4
Source dataset
uspto-grants-1989_07
Patent number
US04846998

Reaction notes

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