Hydrochloric Acid → HCID 17966564, compound

HRID 1630776Notes

Reaction equation

HRID 1630776 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6](SC)=[C:7]([CH:10]=1)[C:8]#[N:9].O[O:14][S:15]([O-:17])=O.[K+].Cl.[CH3:20]O>O>[OH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([S:15]([CH3:20])(=[O:17])=[O:14])=[C:7]([CH:10]=1)[C:8]#[N:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 17966951HCID 17966951, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 17966564HCID 17966564, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A flask is charged with 5-hydroxymethyl-2-methylsulfanyl-benzonitrile (0.866 g, 4.86 mmol) in a mixture of MeOH (10 mL) and water (10 mL). Oxone (7.47 g, 12.16 mmol) is added and the mixture is stirred at room temperature for 16 h. The residue is acidified to pH 1 using aqueous 1M HCl and then extracted with dichloromethane twice. The organic layer is dried over sodium sulfate and concentrated in vacuo to afford 5-hydroxymethyl-2-methanesulfonyl-benzonitrile as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 3.28 (s, 3H), 4.89 (s, 2H), 7.80 (d, J=8.1 Hz, 1H), 7.95 (s, 1H), 8.18 (d, J=8.1 Hz, 1H).

Workup

  1. extractionextracted with dichloromethane twice
  2. dry with materialThe organic layer is dried over sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7f8da9ddbd3447978de56e91f99472f8
Source dataset
uspto-grants-2014_07
Patent number
US08791141B2

Reaction notes

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