O-Cresol → ((4-Hydroxy-3-methylphenyl)sulfanyl)formonitrile

HRID 408672

Reaction equation

HRID 408672 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[S-:9][C:10]#[N:11].[Na+].[Na+].[Br-].BrBr.C([O-])(O)=O.[Na+]>CO>[CH3:1][C:2]1[CH:7]=[C:6]([S:9][C:10]#[N:11])[CH:5]=[CH:4][C:3]=1[OH:8]

Participants

7

Reactant 5

HCID 335O-CresolHCID 24408BromineHCID 253881Sodium BromideHCID 516871Sodium thiocyanateHCID 516892Sodium Bicarbonate

Product 1

HCID 220928((4-Hydroxy-3-methylphenyl)sulfanyl)formonitrileYield 67.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a 250 ml flask were added 10.8 g o-methylphenol, 26.0 g sodium thiocyanate, 70 ml methanol, added dropwise 100 ml methanol solution containing 10.3 g NaBr, 5.3 ml liquid bromine at 0° C. under N2 atmosphere. The mixture was stirred at room temperature for 3 hours. The mixture was neutralized with saturated NaHCO3 solution, extracted with CH2Cl2 for four times. The extract was dried over anhydrous Na2SO4, filtrated, evaporated and purified by column chromatograph (petroleum ether:ethyl acetate=8:1) to obtain 11.1 g yellow solid, yield 67.27%. 1H-NMR (400 MHz, CDCl3, δ ppm) δ 2.2558 (3H, s), 5.0 (1H, s), 6.8 (1H, d, J=8.4 Hz), 7.3605-7.2631 (1H, m), 7.3542 (1H, s).

Workup

  1. extractionextracted with CH2Cl2 for four times
  2. dry with materialThe extract was dried over anhydrous Na2SO4
  3. filtrationfiltrated
  4. customevaporated
  5. custompurified by column chromatograph (petroleum ether:ethyl acetate=8:1)

Sources & evidence

ORD record
ord-33b17429b9824748931f65f162f6d6d6
Source dataset
uspto-grants-2014_06
Patent number
US08759355B2

Linked notes

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