Hydrochloric Acid → 2-[2-(3-Cyanopropyl)benzyl]-1,3-cyclohexanedione

HRID 839728Notes

Reaction equation

HRID 839728 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]1[CH:19]=[CH:18][CH:17]=[CH:16][C:6]=1[CH2:7][CH:8]1[C:13](=[O:14])[CH2:12][CH2:11][CH2:10][C:9]1=[O:15].[C-:20]#[N:21].[Na+].Cl>CS(C)=O>[C:20]([CH2:2][CH2:3][CH2:4][C:5]1[CH:19]=[CH:18][CH:17]=[CH:16][C:6]=1[CH2:7][CH:8]1[C:13](=[O:14])[CH2:12][CH2:11][CH2:10][C:9]1=[O:15])#[N:21]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8929Sodium CyanideHCID 20305130HCID 20305130, compound

Product 1

HCID 203051122-[2-(3-Cyanopropyl)benzyl]-1,3-cyclohexanedione

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 22 g (0.079 mol) of 2-[2-(3-chloropropyl)benzyl]-1,3-cyclohexanedione 3 and 15.5 g (0.316 mol) of NaCN in 250 ml of dry dimethyl sulfoxide was stirred at 95° C for 3 hours. The reaction was filtered while hot to remove NaCl, and the dimethyl sulfoxide was distilled out under high vacuum. The residue was dissolved in 400 ml H2O, filtered through a diatomaceous earth filter aid (celite) to give a red solution and neutralized by the rapid addition of 40 ml concentrated HCl. The precipitate was recrystallized twice from ethyl acetate to give 16 g of the cyanodione, IIa, mp 143° C.

Workup

  1. filtrationThe reaction was filtered while hot
  2. customto remove NaCl
  3. distillationthe dimethyl sulfoxide was distilled out under high vacuum
  4. dissolutionThe residue was dissolved in 400 ml H2O
  5. filtrationfiltered through a diatomaceous earth
  6. filtrationfilter aid (celite)
  7. customto give a red solution
  8. customThe precipitate was recrystallized twice from ethyl acetate
  9. customto give 16 g of the cyanodione, IIa, mp 143° C.

Sources & evidence

ORD record
ord-b777c9aad23847d5bc47b6a902b28327
Source dataset
uspto-grants-1978_06
Patent number
US04096336

Reaction notes

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