Benzaldehyde → alpha-Cyanobenzyl 2,2,3,3-tetramethylcyclopropanecarboxylate

HRID 839517Notes

Reaction equation

HRID 839517 reaction equation
[CH:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C-:9]#[N:10].[Na+].Cl[CH:13]1[C:16]([CH3:18])([CH3:17])[C:15]([CH3:20])([CH3:19])[C:14]1=[O:21]>CN(C)C=O>[CH3:20][C:15]1([CH3:19])[C:16]([CH3:17])([CH3:18])[CH:13]1[C:14]([O:8][CH:1]([C:9]#[N:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:21]

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 8929Sodium CyanideHCID 11105656Cyclobutanone, 4-chloro-2,2,3,3-tetramethyl-

Product 1

HCID 14580510alpha-Cyanobenzyl 2,2,3,3-tetramethylcyclopropanecarboxylateYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 100 mmol of benzaldehyde, 100 mmol of sodium cyanide and 50 ml of N,N-dimethylformamide was stirred at a temperature of 80° C for 30 min. Then, an amount of 100 mmol of 2-chloro-3,3,4,4-tetramethylcyclobutanone was added over a period of 30 min and stiring was continued for six hours. At the end of this period the reactants were fully converted and alpha-cyanobenzyl 2,2,3,3-tetramethylcyclopropanecarboxylate was obtained in a yield of 65%.

Workup

  1. waitstiring was continued for six hours

Sources & evidence

ORD record
ord-cdab0128e9534c5fb84552fc15632672
Source dataset
uspto-grants-1978_06
Patent number
US04096170

Reaction notes

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