Ethanol → HCID 21432375, compound

HRID 2399084Notes

Reaction equation

HRID 2399084 reaction equation
C[C:2]1([CH2:7][CH2:8][C:9]#[C:10][CH2:11][CH2:12]CC#N)[O:6]CC[O:3]1.[C-:16]#N.[Na+].[CH2:19]([OH:21])[CH3:20]>[OH-].[Na+]>[O:21]=[C:19]([CH3:16])[CH2:20][CH2:12][C:11]#[C:10][CH2:9][CH2:8][CH2:7][C:2]([OH:6])=[O:3]

Participants

5

Reactant 3

HCID 702EthanolHCID 8929Sodium CyanideHCID 21432353HCID 21432353, compound

Product 1

HCID 21432375HCID 21432375, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

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.

Workup

  1. temperatureunder reflux

Sources & evidence

ORD record
ord-437283899a8a43e8a42f439f64300701
Source dataset
uspto-grants-1977_05
Patent number
US04026911

Reaction notes

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