Ethylene Glycol → 6-(7-Hydroxyheptyl)-1,4-dioxaspiro[4.4]nonane-7-carbonitrile

HRID 259198Notes

Reaction equation

HRID 259198 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]1[C:13](=[O:14])[CH2:12][CH2:11][CH:10]1[C:15]#[N:16].[CH2:17](O)[CH2:18][OH:19].C1C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC(S(O)(=O)=O)=CC=1.O>[C:15]([CH:10]1[CH2:11][CH2:12][C:13]2([O:19][CH2:18][CH2:17][O:14]2)[CH:9]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][OH:1])#[N:16]

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 241BenzeneHCID 10340Sodium CarbonateHCID 205429242-(7-Hydroxyheptyl)-3-oxocyclopentanecarbonitrile

Product 1

HCID 205429116-(7-Hydroxyheptyl)-1,4-dioxaspiro[4.4]nonane-7-carbonitrileYield 80.6%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 962WaterSolvent

Procedure

A mixture of 2-(7-hydroxyheptyl)-3-oxocyclopentanecarbonitrile (20 g.), ethylene glycol (5.6 g.), p-toluenesulphonic acid (1 g.) and benzene 160 ml.) was heated to reflux for 210 minutes with continuous removal of water. The mixture was cooled to ambient temperature, anhydrous sodium carbonate was added and, after filtration through a bed of sodium carbonate, the solvent was removed under reduced pressure. The residue was distilled under reduced pressure to give 7-cyano-6-(7-hydroxyheptyl)-1,4-dioxaspiro[4,4]nonane (19.3 g.), b.p. 166° C-182° C./0.1 mm.Hg. This material was used as a starting material in the next stage, as aliquot being redistilled to b.p. 177°-179° C./0.1 mm.Hg for elemental analysis:

Workup

  1. temperature) was heated
  2. filtrationafter filtration through a bed of sodium carbonate
  3. customthe solvent was removed under reduced pressure
  4. distillationThe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-071c9b1f2ed945c9a07e2d9538baf870
Source dataset
uspto-grants-1977_07
Patent number
US04036872

Reaction notes

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