Acetone Cyanohydrin → HCID 10631281, compound

HRID 1871052Notes

Reaction equation

HRID 1871052 reaction equation
[C:1]1(=[N:7][OH:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:9]([O:12]C(C)=C)(=O)[CH3:10].CC(C)(O)[C:18]#[N:19]>C1(C)C=CC=CC=1>[C:9]([O:8][NH:7][C:1]1([C:18]#[N:19])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)(=[O:12])[CH3:10]

Participants

5

Reactant 3

HCID 6406Acetone CyanohydrinHCID 7517Cyclohexanone OximeHCID 7916Isopropenyl acetate

Product 1

HCID 10631281HCID 10631281, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 0.115 g (1 mmole) of cyclohexanone oxime, 0.1 g (1 mmole) of isopropenyl acetate, 0.085 g (1 mmole) of acetone cyanohydrin, 0.045 g (0.1 mmole) of di(η5 -pentamethylcyclopentadienyl)samarium [Cp*2Sm(THF)2 ], and 1 ml of toluene was stirred at 25° C. for 3 hours. 1-acetyloxyamino-1-cyanocyclohexane was formed in the reaction mixture in a 60% yield, and the conversion of cyclohexanone oxime was 72%.

Sources & evidence

ORD record
ord-e03f21d005c247c58e0c19fcdfbc41af
Source dataset
uspto-grants-2000_08
Patent number
US06100419

Reaction notes

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