Ammonia → HCID 21432391, compound

HRID 2399083Notes

Reaction equation

HRID 2399083 reaction equation
[CH3:1][C:2]1([CH2:7][CH2:8][C:9]#[CH:10])[O:6][CH2:5][CH2:4][O:3]1.[Cl:11][CH2:12][CH2:13][CH2:14]Br.ClCCCI.[NH2-].[Li+].N>>[CH3:1][C:2]1([CH2:7][CH2:8][C:9]#[C:10][CH2:14][CH2:13][CH2:12][Cl:11])[O:6][CH2:5][CH2:4][O:3]1

Participants

6

Reactant 5

HCID 222AmmoniaHCID 80061-Bromo-3-chloropropaneHCID 24532Lithium amideHCID 813631-Chloro-3-iodopropaneHCID 10034704HCID 10034704, compound

Product 1

HCID 21432391HCID 21432391, compound

Procedure

In a preferred embodiment of the process, 2-methyl-2-(3-butynyl)-1,3-dioxolane is reacted with 1-chloro-3-bromo-propane or 1-chloro-3-iodo-propane, in the presence of lithium amide in liquid ammonia to obtain 2-methyl-2-(7-chloro-3-heptynyl)-1,3-dioxolane. Conversion of the latter to the nitrile, 2-methyl-2-(7-cyano-3-heptynyl)-1,3-dioxolane, is accomplished by reaction with sodium cyanide in ethanol under reflux. The nitrile is then hydrolyzed in sodium hydroxide to obtain the desired 9-oxo-5-decynoic acid.

Sources & evidence

ORD record
ord-e106f8df78c547d0b234b9e084a25266
Source dataset
uspto-grants-1977_05
Patent number
US04026911

Reaction notes

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