Dimethoxymethane → 4-(Ethylthio)benzyl chloride

HRID 1635964

Reaction equation

HRID 1635964 reaction equation
[Cl-:1].[Al+3].[Cl-].[Cl-].[CH3:5]OCOC.[CH2:10]([S:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH3:11]>ClCCCl>[CH2:10]([S:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:5][Cl:1])=[CH:15][CH:14]=1)[CH3:11]

Participants

5

Reactant 3

HCID 8020DimethoxymethaneHCID 12144(Ethylthio)benzeneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 186738584-(Ethylthio)benzyl chloride

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
5 °C

Procedure

Aluminum chloride (2 g, 15 mmol) was suspended in 8 mL 1,2-dichloroethane and the solution was cooled to 5° C. Dimethoxymethane (0.69 mL, 7.8 mmol) over 10 min. Ethylphenylsulfide (0.88 mL, 6.5 mmol) was added and the mixture was warmed to rt. After 15 h ice water was added and the mixture was extracted with methylene chloride (3×). The combined organic fractions were dried over magnesium sulfate and concentrated. The crude material was used directly in the next step.

Workup

  1. temperaturethe mixture was warmed to rt
  2. extractionthe mixture was extracted with methylene chloride (3×)
  3. dry with materialThe combined organic fractions were dried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-28964c644ded4d8ebef150e94210722b
Source dataset
uspto-grants-2003_01
Patent number
US06511994B2

Linked notes

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