Methane, dichloromethoxy- → 3-Methyl-4-(methylthio)benzaldehyde

HRID 1006504Notes

Reaction equation

HRID 1006504 reaction equation
[Sn](Cl)(Cl)(Cl)Cl.[CH3:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[S:13][CH3:14].[CH3:15][O:16]C(Cl)Cl>ClCCl>[CH3:6][C:7]1[CH:12]=[C:11]([CH:10]=[CH:9][C:8]=1[S:13][CH3:14])[CH:15]=[O:16]

Participants

5

Reactant 3

HCID 21004Methane, dichloromethoxy-HCID 24287Tin tetrachlorideHCID 2597431-Methyl-2-(methylsulfanyl)benzene

Product 1

HCID 226713353-Methyl-4-(methylthio)benzaldehydeYield 54%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tin (IV) chloride (13.6 ml, 0.116 mol) was added to an ice-bath cooled solution of 1-methyl-2-(methylthio)benzene (10 g, 0.073 mol) in anhydrous dichloromethane (200 ml) under nitrogen and stirred for a further 2 hours at 0° C. α,α-Dichloromethyl methyl ether (6.56 ml, 0.073 mol) was introduced and the reaction stirred for 1 hour at <10° C. before the cooling was removed. After attaining room temperature, the reaction mixture was poured into ice/water (400 ml), stirred and then extracted with dichloromethane (×3). The combined organic layers were dried over anhydrous magnesium sulfate, filtered, concentrated onto silica gel and purified by flash chromatography, eluting with diethyl ether/isohexane (10:1) to yield the sub-title compound as a brown oil (6.54 g) in 54% yield.

Workup

  1. additionwas introduced
  2. customwas removed
  3. customAfter attaining room temperature
  4. additionthe reaction mixture was poured into ice/water (400 ml)
  5. stirringstirred
  6. extractionextracted with dichloromethane (×3)
  7. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated onto silica gel
  10. custompurified by flash chromatography
  11. washeluting with diethyl ether/isohexane (10:1)

Sources & evidence

ORD record
ord-c9b0bcf9b6744993853cc63a86216900
Source dataset
uspto-grants-2004_09
Patent number
US06790850B1

Reaction notes

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