2-Mercaptophenylacetic acid → 2-[2-(Methyldisulfanyl)phenyl]acetic acid

HRID 2261709Notes

Reaction equation

HRID 2261709 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=[O:10].[CH3:12][S:13](=S)(OC)=O>O.C(O)C.CCOCC>[CH3:12][S:13][S:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=[O:10]

Participants

6

Reactant 2

HCID 51275252-Mercaptophenylacetic acidHCID 14573333Methyl methylthiosulphonate

Product 1

HCID 860666102-[2-(Methyldisulfanyl)phenyl]acetic acidYield 100.7%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of (2-mercaptophenyl)acetic acid (449 mg) in H2O (15 mL) and ethanol (7 mL) was added methyl methanethiosulfonate (372 mg, 2.93 mmol). After stirring for 20 hours, the reaction mixture was diluted with ether and washed with 1 N KOH twice. The water layers were combined and acidified to pH 2 with 5 N hydrochloric acid. This solution was extracted with CH2Cl2 three times. The organic layers were combined, dried over anhydrous MgSO4, filtered, and concentrated in vacuo to afford 576 mg (100% yield) of the (2-methyl disulfanylphenyl)acetic acid product in the form of a yellow oil: 1H NMR (400 MHz, CDCl3) δ (ppm): 2.42 (s, 3H), 3.92 (s, 2H), 7.10-7.40 (m, 3H), 7.80 (d, J=7.6 Hz, 1H), 10.34 (s, 1H); 13C NMR (100 MHz, CDCl3) δ (ppm): 22.7, 38.9, 127.8, 128.1, 128.3, 128.8, 130.4, 130.8, 130.9, 177.1. HRMS (EI): m/e calcd. for C9H10O2S2: 214.012223, Found: 214.012637 (Δ=−1.9 ppm).

Workup

  1. washwashed with 1 N KOH twice
  2. extractionThis solution was extracted with CH2Cl2 three times
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-77e6d1b39c0e4c40aba945204d037502
Source dataset
uspto-grants-2010_12
Patent number
US07847119B2

Reaction notes

Loading…