Hydrochloric Acid → 2-Hydroxy-6-propylsulfanylbenzonitrile

HRID 1983979Notes

Reaction equation

HRID 1983979 reaction equation
CC1[C:7]([S:8][CH2:9][CH2:10][CH3:11])=[CH:6][CH:5]=CC=1[N+]([O-])=O.N(OCCCC)=O.[CH3:22][C:23](C)([O-:25])[CH3:24].[K+].Cl.[CH3:29][N:30](C)C=O>>[OH:25][C:23]1[CH:24]=[CH:5][CH:6]=[C:7]([S:8][CH2:9][CH2:10][CH3:11])[C:22]=1[C:29]#[N:30]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 6228Dimethylformamide2×HCID 10996Butyl nitriteHCID 23665647Potassium tert-butoxideHCID 685664672-Methyl-1-nitro-3-propylsulfanylbenzene

Product 1

HCID 685669922-Hydroxy-6-propylsulfanylbenzonitrile

Procedure

30 g (0.14 mol) of 2-methyl-1-nitro-3-propylsulfanylbenzene, 18.9 g (0.18 mol) of n-butyl nitrite were dissolved in 120 ml of dimethylformamide and cooled to (−20)° C. Then a solution of potassium t-butoxide in 120 ml of DMF is added dropwise over the course of 25 min. After the reaction mixture had been stirred at (−25)° C. for one hour, it was stirred into a mixture of ice and 150 ml of concentrated hydrochloric acid. The mixture was warmed to room temperature, and the resulting solid was filtered off with suction and washed several times with water and once with cyclohexane. The solid was purified by stirring with a little amount of methylene chloride. Yield: 12.4 g (46% of theory) of the desired product. 1H NMR (in CDCl3): δ=1.05 ppm (t, 3H, aliph. Me), 1.7 ppm (m, 2H, aliph. CH2), 3.0 ppm (t, 2H, S CH2), 6.8 ppm (d, 1H, arom. H), 6.9 ppm (d, 1H, arom. H), 7.35 ppm (m, 1H, arom. H).

Workup

  1. temperaturecooled to (−20)° C
  2. filtrationthe resulting solid was filtered off with suction
  3. washwashed several times with water
  4. customThe solid was purified
  5. stirringby stirring with a little amount of methylene chloride

Sources & evidence

ORD record
ord-8184e70da77d4ea788b2540ba5d6a758
Source dataset
uspto-grants-2009_06
Patent number
US07544637B2

Reaction notes

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