Hydrochloric Acid → HCID 12856162, compound

HRID 1073478Notes

Reaction equation

HRID 1073478 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2Cl)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[CH3:14][N:15]1CCCC1=O.Cl>O>[C:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:14]#[N:15])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 13387N-methyl-2-pyrrolidoneHCID 128155702'-Chloro-2,3,4,5-tetrahydro-1,1'-biphenyl

Product 1

HCID 12856162HCID 12856162, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 19.3 g. (0.1 mol) o-(1-cyclohexenyl)-chlorobenzene and 16.4 g. (0.18 mol) cuprous cyanide in 100 ml. N-methylpyrrolidinone was heated to 200° C. for 15 hours. For working up, the brown-black product was introduced into a solution of 40 g. ferric chloride, 10 ml. concentrated hydrochloric acid and 60 ml. water and the mixture heated for 0.5 hours to 60° to 70° C. The N-methylpyrrolidinone phase was separated off and the aqueous phase was extracted several times with toluene. The combined organic phases were successively washed with 2N hydrochloric acid, water and 10% aqueous sodium hydroxide solution and subsequently dried with anhydrous sodium sulphate and evaporated. Fractional distillation gave the desired benzonitrile derivative. Yield 68% of theory; b.p. 90-92° C./0.1 mm.Hg; nD26 =1.5648.

Workup

  1. additionA mixture of 19.3 g
  2. additionthe brown-black product was introduced into a solution of 40 g
  3. customThe N-methylpyrrolidinone phase was separated off
  4. extractionthe aqueous phase was extracted several times with toluene
  5. washThe combined organic phases were successively washed with 2N hydrochloric acid, water and 10% aqueous sodium hydroxide solution
  6. dry with materialsubsequently dried with anhydrous sodium sulphate
  7. customevaporated
  8. distillationFractional distillation
  9. customgave the desired benzonitrile derivative

Sources & evidence

ORD record
ord-27c11c78b78d4616b12c693754a1a7dd
Source dataset
uspto-grants-1990_11
Patent number
US04970077

Reaction notes

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