4-Methylbenzenethiol → Ethyl 2,2-bis(4-methylthiophenoxy)acetate

HRID 28115

Reaction equation

HRID 28115 reaction equation
[Na].[CH3:2][C:3]1[CH:8]=[CH:7][C:6]([SH:9])=[CH:5][CH:4]=1.Cl[CH:11](Cl)[C:12]([O:14][CH2:15][CH3:16])=[O:13]>CO.C(OCC)C>[CH3:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][CH:11]([S:9][C:6]2[CH:7]=[CH:8][C:3]([CH3:2])=[CH:4][CH:5]=2)[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 78114-MethylbenzenethiolHCID 10808Ethyl dichloroacetateHCID 5360545Sodium

Product 1

HCID 13107767Ethyl 2,2-bis(4-methylthiophenoxy)acetateYield 68%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent3×HCID 3283Diethyl EtherSolvent

Conditions

Temperature
20 °C

Procedure

Sodium (3.54 g) is dissolved in methanol (140 cc) and a solution of 4-methylthiophenol (21.8 g) in methanol (25 cc) is added. The mixture is stirred for 1 hour at 20° C. and a solution of ethyl dichloroacetate (12.5 g) in methanol (30 cc) is then added. The mixture is allowed to cool, the white precipitate obtained is filtered off, and the filtrate is concentrated to dryness under reduced pressure (20 mmHg) at 40° C. The oil obtained is taken up in diethyl ether (250 cc) and washed four times with N sodium hydroxide solution (50 cc each time) and four times with distilled water (50 cc each time). The ethereal phase is dried over anhydrous sodium sulphate, filtered, treated with animal charcoal, filtered and concentrated to dryness under reduced pressure (20 mmHg) at 40° C. Ethyl 2,2-bis(4-methylthiophenoxy)acetate (18 g) is thus obtained as a yellow oil.

Workup

  1. temperatureto cool
  2. customthe white precipitate obtained
  3. filtrationis filtered off
  4. concentrationthe filtrate is concentrated to dryness under reduced pressure (20 mmHg) at 40° C
  5. customThe oil obtained
  6. washwashed four times with N sodium hydroxide solution (50 cc each time) and four times with distilled water (50 cc each time)
  7. dry with materialThe ethereal phase is dried over anhydrous sodium sulphate
  8. filtrationfiltered
  9. additiontreated with animal charcoal
  10. filtrationfiltered
  11. concentrationconcentrated to dryness under reduced pressure (20 mmHg) at 40° C

Sources & evidence

ORD record
ord-6bb31a9cb3cd4b5eaac488e1d6f003df
Source dataset
uspto-grants-1980_09
Patent number
US04225589

Linked notes

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