Hydrochloric Acid → HCID 19828053, compound

HRID 638228Notes

Reaction equation

HRID 638228 reaction equation
[C:1]([C:3](=[CH:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH3:18])=[CH:12][CH:11]=1)[C:4]([O:6][CH2:7]C)=[O:5])#[N:2].[Mg].Cl>CO>[C:1]([CH:3]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH3:18])=[CH:12][CH:11]=1)[C:4]([O:6][CH3:7])=[O:5])#[N:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5462224MagnesiumHCID 54309886HCID 54309886, compound

Product 1

HCID 19828053HCID 19828053, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
30 °C

Procedure

A mixture of 20.50 g (84.3 mmole) of the product of Part (i), 8.75 g magnesium turnings and 200 ml methanol was stirred under a nitrogen atmosphere for six hours with periodic cooling to maintain a temperature of about 30° C. The mixture was acidified with hydrochloric acid, extracted with ethyl ether, the extracts washed with sodium bicarbonate solution, water, brine and dried over MgSO4. Evaporation of solvent gave 23.8 g of crude product which was purified by column chromatography on silica gel, eluting with methylene chloride to provide 11.55 g (59%) of purified methyl 2-cyano-3-(4-n-propylphenyl)propionate. This was combined with 4.17 g sodium chloride, 175 ml dimethylsulfoxide and 5 ml water under nitrogen and the mixture heated at 150° C. for five hours. The reaction mixture was cooled, poured into 700 ml water and extracted with 2×500 ml ethyl acetate. The combined extracts were washed with brine (300 ml) dried over anhydrous sodium sulfate and concentrated in vacuo to give 12.5 g of the desired nitrile which was purified by distillation, b.p. 124°-128° C. (1.0 mm). 1H-NMR(CDCl3)ppm(delta): 0.75-1.15 (t, 3H), 1.30-2.00 (m, 2H), 2.40-3.10 (m, 6H), 7.15 (s, 4H).

Workup

  1. temperaturewith periodic cooling
  2. extractionextracted with ethyl ether
  3. washthe extracts washed with sodium bicarbonate solution, water, brine
  4. dry with materialdried over MgSO4
  5. customEvaporation of solvent
  6. customgave 23.8 g of crude product which
  7. customwas purified by column chromatography on silica gel
  8. washeluting with methylene chloride

Sources & evidence

ORD record
ord-97aea7f7af0a4351a097ca4c7d6bb894
Source dataset
uspto-grants-1985_12
Patent number
US04560690

Reaction notes

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