Hydrochloric Acid → HCID 9837354, compound

HRID 647913Notes

Reaction equation

HRID 647913 reaction equation
[CH:1]([C:3]1[C:15]([O:16]C)=[CH:14][CH:13]=[CH:12][C:4]=1[O:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]#[N:11])=[O:2].[I-].[Mg+2].[I-].Cl>O1CCCC1.CCOCC>[CH:1]([C:3]1[C:15]([OH:16])=[CH:14][CH:13]=[CH:12][C:4]=1[O:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]#[N:11])=[O:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 5462737Magnesium diiodideHCID 20484345HCID 20484345, compound

Product 1

HCID 9837354HCID 9837354, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 5-(2-formyl-3-methoxyphenoxy)pentanonitrile (2.33 g, 0.01 M) in dry tetrahydrofuran (28 ml) was added dropwise a solution of magnesium iodide (4.17 g, 0.015 M) in dry ether (55 ml). The mixture was then stirred under reflux (51/2 hr). The cooled mixture was poured into 10% hydrochloric acid (50 ml). The organic layer was separated and the aqueous phase extracted with ethyl acetate. The combined organic solutions were washed with water and extracted quickly with 2 N sodium hydroxide solution (1×25 ml). The separated aqueous phase was immediately acidified with concentrated hydrochloric acid with cooling and the solid produced filtered off and washed with water to give 5-(2-formyl-3-hydroxyphenoxy)pentanonitrile, m.p. 66°-67° C. from benzene/petrol.

Workup

  1. temperatureunder reflux (51/2 hr)
  2. customThe organic layer was separated
  3. extractionthe aqueous phase extracted with ethyl acetate
  4. washThe combined organic solutions were washed with water
  5. extractionextracted quickly with 2 N sodium hydroxide solution (1×25 ml)
  6. temperaturewith cooling
  7. customthe solid produced
  8. filtrationfiltered off
  9. washwashed with water

Sources & evidence

ORD record
ord-4b81c74433674158b509fc15a3e2214b
Source dataset
uspto-grants-1983_10
Patent number
US04410537

Reaction notes

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