Hydrochloric Acid → HCID 17966564, compound

HRID 1661551Notes

Reaction equation

HRID 1661551 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-99389f3c76094a4ba9af05c84314e4c0
Source dataset
uspto-grants-2011_10
Patent number
US08030334B2

Reaction notes

Loading…