Benzyl Chloride → Benzyl 2-cyanoacetate

HRID 1979096Notes

Reaction equation

HRID 1979096 reaction equation
[C:1]([CH2:3][C:4]([OH:6])=[O:5])#[N:2].[OH-].[Na+].[CH2:9](Cl)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.COC(C)(C)C.O>[C:1]([CH2:3][C:4]([O:6][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:5])#[N:2]

Participants

6

Reactant 3

HCID 7503Benzyl ChlorideHCID 9740Cyanoacetic acidHCID 14798Sodium Hydroxide2×

Product 1

HCID 560818Benzyl 2-cyanoacetateYield 70%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 23212559water MeOtBuSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 1.7 g (0.02 mol) of cyanoacetic acid, 0.8 g (0.02 mol) of sodium hydroxide, 7.60 g (0.06 mol, 3 equivalents) of benzyl chloride and 0.64 g (2.0 mmol) of tetrabutylammonium bromide in 15 ml of tert-butyl methyl ether/water (v:v=2:1 ) was stirred at 100° C. (oil bath temperature 110° C.) for 3 h. The pH of the aqueous phase was then adjusted from 0.2 to 6.3 using 3.15 g of 1 M aqueous sodium hydroxide solution, the organic phase was separated off and the aqueous phase was extracted with tert-butyl methyl ether (2×5 ml). The combined organic phases was dried with sodium sulfate and analyzed by gas chromatography. 2.45 g (70 percent) of benzyl cyanoacetate was obtained.

Workup

  1. customthe organic phase was separated off
  2. extractionthe aqueous phase was extracted with tert-butyl methyl ether (2×5 ml)
  3. dry with materialThe combined organic phases was dried with sodium sulfate

Sources & evidence

ORD record
ord-a200f8e3e7e74e3084ff199f8b0230df
Source dataset
uspto-grants-2001_05
Patent number
US06239307B1

Reaction notes

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