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

HRID 839516Notes

Reaction equation

HRID 839516 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].CCCCCCC>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

6

Reactant 4

HCID 240BenzaldehydeHCID 5975CyanideHCID 8900HeptaneHCID 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
70 °C

Procedure

A 50-ml round-bottomed 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 a cyanide, 20 ml of n-heptane and 1 ml of water. The rection mixture was stirred vigorously at a temperature of 70° C. Two experiments were carried out in this manner. Table III states the cyanides used and presents the yields of the alpha-cyanobenzyl 2,2,3,3-tetramethylcyclopropane-carboxylate formed.

Workup

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

Sources & evidence

ORD record
ord-c71f71ca261c4c61a5ecc80566ca7d49
Source dataset
uspto-grants-1978_06
Patent number
US04096170

Reaction notes

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