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

HRID 372046Notes

Reaction equation

HRID 372046 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]>C1(C)C=CC(S(O)(=O)=O)=CC=1.C1C=CC=CC=1>[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

5

Reactant 2

HCID 174Ethylene GlycolHCID 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 241BenzeneSolvent

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 31/2 hours 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°-182° C./0.1 mm.Hg. This material was used as a starting material in the next stage, an aliquot being redistilled to b.p. 177°-179° C./0.1 mm.Hg for elemental analysis:

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 31/2 hours
  3. customwith continuous removal of water
  4. additionanhydrous sodium carbonate was added
  5. filtrationafter filtration through a bed of sodium carbonate
  6. customthe solvent was removed under reduced pressure
  7. distillationThe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-58530d23ae634c97bc4a9beaf267aa40
Source dataset
uspto-grants-1978_05
Patent number
US04088695

Reaction notes

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