Water → Lactonitrile

HRID 1105722Notes

Reaction equation

HRID 1105722 reaction equation
[N:1]1C=C[CH:4]=[CH:3][CH:2]=1.[Cl:7][C:8]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[C:9]=1[C:10](Cl)=[O:11].[OH2:18]>>[OH:11][CH:3]([CH3:4])[C:2]#[N:1].[Cl:7][C:8]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[C:9]=1[C:10]([O:18][CH2:4][CH2:3][C:2]#[N:1])=[O:11]

Participants

5

Reactant 3

HCID 962WaterHCID 1049PyridineHCID 783922,6-Dichlorobenzoyl chloride

Product 2

HCID 6572LactonitrileHCID 12832599HCID 12832599, compound

Procedure

A solution of 3.7 grams (0.052 mole) of 2-hydroxypropionitrile in 8.9 grams (0.10 mole) of pyridine was prepared. To this stirred solution at ambient temperature was added 10.4 grams (0.05 mole) of 2,6-dichlorobenzoyl chloride dropwise during a 20 minute period. The exothermic reaction caused the temperature of the reaction mixture to rise to 50°. The reaction mixture was heated at 75°-80° for 75 minutes. The cooled reaction mixture was poured into 150 ml of water and the mixture was stirred. The mixture was extracted with 200 ml of diethyl ether. The extract was washed with three portions of 30 ml each of an aqueous solution of 3% hydrochloric acid, then three portions of 30 ml each of water. The organic layer was dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to an amber oil. The oil solidified and the solid was recrystallized from hexane-diethyl ether to give an oily semi-solid. The semi-solid and mother liquor were combined and concentrated under reduced pressure to an oil. An attempt to sublime the oil failed. The oil was distilled under reduced pressure using a short-path distilling system to give 3.1 grams of 2-cyanoethyl 2,6-dichlorobenzoate; bp 117°/0.005 mm. The oil product solidified; mp 45°-46° C. The nmr and the ir spectra were consistent with the proposed structure.

Workup

  1. customThe exothermic reaction
  2. customto rise to 50°
  3. temperatureThe reaction mixture was heated at 75°-80° for 75 minutes
  4. customThe cooled reaction mixture
  5. extractionThe mixture was extracted with 200 ml of diethyl ether
  6. washThe extract was washed with three portions of 30 ml each of an aqueous solution of 3% hydrochloric acid
  7. dry with materialThe organic layer was dried with sodium sulfate
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated under reduced pressure to an amber oil
  10. customthe solid was recrystallized from hexane-diethyl ether
  11. customto give an oily semi-solid
  12. concentrationconcentrated under reduced pressure to an oil
  13. distillationThe oil was distilled under reduced pressure

Sources & evidence

ORD record
ord-966184c12e5b439d98d67fb31ef19e49
Source dataset
uspto-grants-1982_01
Patent number
US04309566

Reaction notes

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