Benzyltrimethylammonium hydroxide → 2-(2-Methanesulfinyl-2-methylsulfanyl-vinyl)-1,3-dimethyl-benzene

HRID 60191

Reaction equation

HRID 60191 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:3]=1[CH:4]=O.[CH3:11][S:12]([CH2:14][S:15][CH3:16])=[O:13].[OH-].C([N+](C)(C)C)C1C=CC=CC=1>O1CCOCC1>[CH3:11][S:12]([C:14]([S:15][CH3:16])=[CH:4][C:3]1[C:2]([CH3:1])=[CH:9][CH:8]=[CH:7][C:6]=1[CH3:10])=[O:13]

Participants

5

Reactant 3

HCID 66854Benzyltrimethylammonium hydroxideHCID 99129Methyl (methylsulfinyl)methyl sulfideHCID 5838412,6-Dimethylbenzaldehyde

Product 1

HCID 866312652-(2-Methanesulfinyl-2-methylsulfanyl-vinyl)-1,3-dimethyl-benzeneYield 68.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2,6-dimethyl-benzaldehyde (14.6 g, 109 mmol) in 1,4-dioxane (24.7 mL) was added methyl methylsulfinylmethyl sulfide (13.5 g, 109 mmol) followed by benzyltrimethylammonium hydroxide (9.10 g, 54.4 mmol). The resulting mixture was heated at 80° C. After 16 h, the mixture was cooled to rt and concentrated. The resulting residue was purified by FCC to afford a yellow oil (17.9 g, 68%). MS (ESI): mass calcd. for C12H16OS2, 240.1; m/z found, 241.1 [M+H]+. 1H NMR (CDCl3): 7.71 (s, 1H), 7.19-7.13 (m, 1H), 7.07 (d, J=7.5 Hz, 2H), 2.82 (s, 3H), 2.24 (s, 6H), 2.06 (s, 3H).

Workup

  1. temperaturethe mixture was cooled to rt
  2. concentrationconcentrated
  3. customThe resulting residue was purified by FCC

Sources & evidence

ORD record
ord-4f5865c9b645451dbc571947ad8f366c
Source dataset
uspto-grants-2016_09
Patent number
US09440978B2

Linked notes

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