Diethyl Ether → 1-[(2,2-Diethoxyethyl)thio]-3-methylbenzene

HRID 1007944Notes

Reaction equation

HRID 1007944 reaction equation
[C:1]1(C)[C:2]([SH:7])=[CH:3][CH:4]=[CH:5][CH:6]=1.[OH-].[K+].[CH2:11]([O:13][CH:14]([O:17][CH2:18][CH3:19])[CH2:15]Br)[CH3:12].[CH2:20](OCC)C>C(O)C>[CH2:11]([O:13][CH:14]([O:17][CH2:18][CH3:19])[CH2:15][S:7][C:2]1[CH:1]=[CH:6][CH:5]=[C:4]([CH3:20])[CH:3]=1)[CH3:12]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 87122-ThiocresolHCID 14797Potassium HydroxideHCID 74852Ethane, 2-bromo-1,1-diethoxy-

Product 1

HCID 226664661-[(2,2-Diethoxyethyl)thio]-3-methylbenzene

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 90 mL of ethanol is dissolved 25 g of toluenethiol, to which are added 12.42 g of potassium hydroxide and 33.3 mL of bromoacetaldehyde diethyl acetal. The mixture thus obtained is heated under reflux for 2.5 hours. The reaction mixture is introduced into a mixture of ice water and diethyl ether, and the organic layer is separated. The organic layer is washed with saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, the solvent is distilled off under reduced pressure, and the residue is distilled under reduced pressure (113-125° C./2.5 mm Hg) to obtain 41.5 g of 1-[(2,2-diethoxyethyl)sulfanyl]-3-methylbenzene as an oily product.

Workup

  1. customThe mixture thus obtained
  2. temperatureis heated
  3. temperatureunder reflux for 2.5 hours
  4. customthe organic layer is separated
  5. washThe organic layer is washed with saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent is distilled off under reduced pressure
  8. distillationthe residue is distilled under reduced pressure (113-125° C./2.5 mm Hg)

Sources & evidence

ORD record
ord-0ae847df7b214c3183512f7eaf62abbd
Source dataset
uspto-grants-2004_09
Patent number
US06797726B1

Reaction notes

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