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

HRID 839515Notes

Reaction equation

HRID 839515 reaction equation
[CH:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH:10]1[C:13]([CH3:15])([CH3:14])[C:12]([CH3:17])([CH3:16])[C:11]1=[O:18].[C-:19]#[N:20].[Na+]>O>[CH3:17][C:12]1([CH3:16])[C:13]([CH3:14])([CH3:15])[CH:10]1[C:11]([O:8][CH:1]([C:19]#[N:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:18]

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-tetramethylcyclopropanecarboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
23 °C

Procedure

A 50ml round-buttomed flask provided with a magnetic stirrer was charged with 10 mmol of benzaldehyde, 10 mmol of 2-chloro-3,3,4,4-tetramethylcyclobutanone, 12 mmol of sodium cyanide, 20 ml of a solvent and 1 ml of water. The reaction mixture was stirred vigorously at a temperature of 23° C. Two experiments ware carried out in this manner. Table II states the solvents used and presents the yields of the alpha-cyanobenzyl 2,2,3,3-tetramethylcyclopropanecarboxylate formed.

Workup

  1. customA 50ml round-buttomed flask provided with a magnetic stirrer

Sources & evidence

ORD record
ord-ad5b8ef185b843ffadb5fa0287118b04
Source dataset
uspto-grants-1978_06
Patent number
US04096170

Reaction notes

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