Synthesis of gamma-decalactone from 1-octene and iodoacetic acid ethyl ester

Synthesis of gamma-decalactone from 1-octene and iodoacetic acid ethyl ester

 gamma-Decalactone
1-Octene + Iodoacetic acid ethyl ester
Cu
reacts to
 

gamma-Decalactone

+    

Iodoethane

Synthesis of gamma-decalactone from 1-octene and iodoacetic acid ethyl ester

(batch scale 10 mmol)

Substances
1-octen (bp 121 °C) 1.12 g (1.56 mL, 10.0 mmol)
iodoacetic acid ethyl ester (bp 73-74 °C/ 21 hPa) 2.78 g (1.54 mL, 13.0 mmol)
copper powder (finely powdered, > 230 mesh ASTM) 1.53 g (24.0 mmol)
tert-butyl methyl ether (bp 55 °C) 35 mL
Reaction
In a 50 mL two-neck flask with magnetic stir bar and a reflux condenser connected with a
protective gas piping 1.12 g (1.56 mL, 10.0 mmol) 1-octen are mixed with 2.78 g (1.54 mL,
13.0 mmol) iodoacetic acid ethyl ester and 1.53 g (24.0 mmol) copper powder under a
protective gas atmosphere. Afterwards the reaction mixture is stirred at 130 °C oil bath
temperature under protective gas for 2 hours under reflux. NOP http://www.oc-praktikum.de

Work up
The reaction mixture is cooled down to room temperature, diluted with 20 mL tert-butyl
methyl ether, stirred for 5 minutes and filtered off. The copper powder on the filter is washed
three times with 5 mL tert-butyl methyl ether each. Filtrate and wash solutions are combined,
the solvent is evaporated at the rotary evaporator. A liquid residue remains as crude product.
Crude yield: 1.5 g
The crude product is fractional distilled in a half-micro distillation apparatus under reduced
pressure.
Yield: 1.30 g ( 7.63 mmol, 77%); head temperature 85 °C (4.8·10-2 hPa, oil bath temperature
120 °C), colourless liquid; 20 nD = 1.4508

 

1H NMR

1H-NMR: gamma-Decalactone
500 MHz, CDCl3
delta [ppm] mult. atoms assignment
0.74 t 3 H 10-H
1.12-1.20 m 8 H 6-H, 7-H, 8-H, 9-H
1.39-1.77 m 3 H 3-H, 5-Hb
2.18 m 1 H 5-Ha
2.36 dd 2 H 2-H
4.33 tt 1 H 4-H
7.26     CHCl3

13C NMR

 
13C-NMR: gamma-Decalactone
125.7 MHz, CDCl3
delta [ppm] assignment
13.9 C10
22.4 C9
25.0 C5
27.9-29.0 C6, C7, C8
31.5 C3
35.4 C2
80.9 C4
177.1 C1 (O-C(=O)-)
76.5-77.5 CDCl3

IR

 
IR: gamma-Decalactone[Film, T%, cm-1][cm-1]assignment

Instruction (batch scale 100 mmol)
Equipment
100 mL two-neck flask, protective gas supply, reflux condenser, heatable magnetic stirrer,
magnetic stir bar, rotatory evaporator, high vacuum pump, distillation apparatus, oil bath
Substances
1-octen (bp 121 °C) 11.2 g (15.6 mL, 100 mmol)
iodoacetic acid ethyl ester (bp 73-74 °C/ 21 hPa) 27.8 g (15.4 mL, 130 mmol)
copper powder (finely powdered, > 230 mesh ASTM) 15.3 g (240 mmol)
tert-butyl methyl ether (bp 55 °C) 130 mL
 NOP http://www.oc-praktikum.de

Reaction
In a 100 mL two-neck flask with magnetic stir bar and a reflux condenser connected with a
protective gas piping 11.2 g (15.6 mL, 100 mmol) 1-octen are mixed with 27.8 g (15.4 mL,
130 mmol) iodoacetic acid ethyl ester and 15.1 g (240 mmol) copper powder under a protectiv
gas atmosphere. Afterwards the reaction mixture is stirred at 130 °C oil bath temperature
under protective gas for 6 hours under reflux.
Work up
The reaction mixture is cooled down to room temperature, diluted with 30 mL tert-butyl
methyl ether, stirred for 5 minutes and filtered off. The copper powder on the filter is washed
4 times with 25 mL tert-butyl methyl ether each. Filtrate and wash solutions are combined,
the solvent is evaporated at the rotary evaporator. A liquid residue remains as crude product.
Crude yield: 15.9 g
The crude product is fractional distilled under reduced pressure.
Yield: 13.5 g (79.3 mmol, 79%); head temperature 70 °C (1.7·10-2 hPa, oil bath temperature
120 °C), colourless liquid; 20 nD = 1.4508 

 
 
 
 

Equipment

Batch scale:   0.01 mol   0.1 mol 1-Octene
two-necked flask 50 mL two-necked flask 50 mL   protective gas piping protective gas piping
reflux condenser reflux condenser   heatable magnetic stirrer with magnetic stir bar heatable magnetic stirrer with magnetic stir bar
rotary evaporator rotary evaporator   vacuum pump vacuum pump
semi-micro distillation apparatus semi-micro distillation apparatus   oil bath oil bath
 

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