N-methyl-2-pyrrolidone → HCID 13548200, compound

HRID 1577057Notes

Reaction equation

HRID 1577057 reaction equation
Br[C:2]1[CH:3]=[C:4]([OH:12])[CH:5]=[CH:6][C:7]=1[CH2:8][CH2:9][CH2:10][CH3:11].[CH3:13][N:14]1CCCC1=O>Cl.O>[C:13]([C:2]1[CH:3]=[C:4]([OH:12])[CH:5]=[CH:6][C:7]=1[CH2:8][CH2:9][CH2:10][CH3:11])#[N:14]

Participants

5

Reactant 2

HCID 13387N-methyl-2-pyrrolidoneHCID 20571557HCID 20571557, compound

Product 1

HCID 13548200HCID 13548200, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Procedure

16.0 g (0.07 mol) of the 3-bromo-4-n-butylphenol prepared in Step IV was dissolved in 70 ml of N-methyl-2-pyrrolidone. 6.5 g (0.073 mol) cuprous cyanide was added to the suspension which was refluxed for four hours. The reaction mixture was cooled to room temperature and poured into a solution of 26 g ferric chloride hexahydrate dissolved in a mixed solution of 10 ml of concentrated hydrochloric acid and 47 ml of water. The resultant solution was stirred with heating for 30 minutes at 65° C. in order to decompose nitrile complexes with cuprous bromide. Next, the suspension was poured into 300 ml of cold water, and an organic layer which separated out was extracted with ether. After the organic layer was clearned with acid, alkali and water and was dehydrated with anhydrous sodium sulfate, ether in the organic layer was distilled off. The residue was distilled under vacuum (115° C./1 mmHg) to yield 8.4 g of purified 3-cyano-4-n-butylphenol. The yield was calculated to be 68.2%.

Workup

  1. temperaturewas refluxed for four hours
  2. temperaturewith heating for 30 minutes at 65° C. in order
  3. customan organic layer which separated out
  4. extractionwas extracted with ether
  5. distillationwas distilled off
  6. distillationThe residue was distilled under vacuum (115° C./1 mmHg)

Sources & evidence

ORD record
ord-53668cf9f42548bcbe4a39dab338c2bb
Source dataset
uspto-grants-1981_09
Patent number
US04287085

Reaction notes

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