Water → 4-Methoxy-o-phenylenediacetonitrile

HRID 224563Notes

Reaction equation

HRID 224563 reaction equation
[C-:1]#[N:2].[Na+].[CH3:4][O:5][C:6]1[CH:7]=[C:8]([CH2:14]Br)[C:9]([CH2:12]Br)=[CH:10][CH:11]=1.[C-:16]#[N:17].O>CS(C)=O>[CH3:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:1]#[N:2])=[C:8]([CH2:14][C:16]#[N:17])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 5975CyanideHCID 8929Sodium CyanideHCID 105417861,2-Bis(bromomethyl)-4-methoxybenzene

Product 1

HCID 705925414-Methoxy-o-phenylenediacetonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

Finely ground sodium cyanide (73 gm., 1.48 m) was suspended in dimethylsulfoxide (500 ml.) by means of a "Vibro-Mixer". A solution of 4-Methoxy-α,α'-dibromo-o-xylene (113 gm., 0.384 m) in dimethylsulfoxide (200 ml.) was added dropwise to the cyanide suspension. The internal temperature was kept at 35°-38° C. by means of an ice bath. The addition took 15 minutes. Agitation of the reaction was continued for a further 11/2 hours. The reaction mixture was poured into water (4 l.). The aqueous mixture was extracted with ether (2×1 l., 3×500 ml.) and the combined ether extracts were washed with dilute hydrochloric acid (6 N) (2×500 ml.), saturated sodium carbonate solution (1×500 ml.), water (3×500 ml.) and saturated sodium chloride solution (2×500 ml.). The ether layer was dried over magnesium sulfate. The dried ethereal solution was evaporated to an oil which was distilled and the fraction with boiling range 160°- 165° (0.1 mm) was collected. wt.=53 gm. The oil obtained was crystallized from ether (650 ml.) to give 45 gm. (m.p. 51°-53°). A second drop of 5.8 gm.(m.p. 49°-51°) was obtained.

Workup

  1. customThe internal temperature was kept at 35°-38° C. by means of an ice bath
  2. additionThe addition
  3. custom2 hours
  4. extractionThe aqueous mixture was extracted with ether (2×1 l., 3×500 ml.)
  5. washthe combined ether extracts were washed with dilute hydrochloric acid (6 N) (2×500 ml.), saturated sodium carbonate solution (1×500 ml.), water (3×500 ml.) and saturated sodium chloride solution (2×500 ml.)
  6. dry with materialThe ether layer was dried over magnesium sulfate
  7. customThe dried ethereal solution was evaporated to an oil which
  8. distillationwas distilled
  9. customthe fraction with boiling range 160°- 165° (0.1 mm) was collected
  10. customThe oil obtained
  11. customwas crystallized from ether (650 ml.)
  12. customto give 45 gm
  13. custom(m.p. 49°-51°) was obtained

Sources & evidence

ORD record
ord-5c38fa5444ef4dce8659eb61daaf938d
Source dataset
uspto-grants-1980_11
Patent number
US04233217

Reaction notes

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