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

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Cu

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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: 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: 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: 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 

http://kriemhild.uft.uni-bremen.de/nop/en/instructions/pdf/4004_en.pdf

Operating scheme

Equipment

Batch scale:

0.01 mol

0.1 mol

1-Octene

	two-necked flask 50 mL			protective gas piping
	reflux condenser			heatable magnetic stirrer with magnetic stir bar
	rotary evaporator			vacuum pump
	semi-micro distillation apparatus			oil bath