Ethanol → Ethyl (4-methylbenzylthio)acetate

HRID 1074053Notes

Reaction equation

HRID 1074053 reaction equation
[SH:1][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].CC[O-].[Na+].C(O)C.Br[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=1>ClCCl>[CH3:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][S:1][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 7721p-Xylyl bromideHCID 12185Ethyl ThioglycolateHCID 2723922Sodium ethoxide

Product 1

HCID 4107274Ethyl (4-methylbenzylthio)acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl 2-mercaptoacetate (8.5 cc) is added in the course of 15 minutes at a temperature in the region of 20° C. to a stirred solution, through which a stream of nitrogen is passed, of a 2M ethanolic solution of sodium ethylate (37.5 cc) and ethanol (50 cc). The mixture is left with stirring for 15 minutes at the same temperature, and α-bromo-p-xylene (13.9 g) is then added in the course of 20 minutes at a temperature in the region of 20° C. Stirring is maintained for 60 minutes at this temperature, and the reaction mixture is then evaporated to dryness at 50° C. under reduced pressure (20 mm Hg; 2.7 kPa). The residue obtained is dissolved in dichloromethane (100 cc), and the organic phase is dried over anhydrous magnesium sulphate, filtered and concentrated to dryness at 40° C. under reduced pressure (20 mm Hg; 2.7 kPa). Ethyl (4-methylbenzylthio)acetate (15.6 g) is thereby obtained, and is used in the crude state in the subsequent syntheses.

Workup

  1. waitThe mixture is left
  2. additionis then added in the course of 20 minutes at a temperature in the region of 20° C
  3. temperatureis maintained for 60 minutes at this temperature
  4. customthe reaction mixture is then evaporated to dryness at 50° C. under reduced pressure (20 mm Hg; 2.7 kPa)
  5. customThe residue obtained
  6. dry with materialthe organic phase is dried over anhydrous magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness at 40° C. under reduced pressure (20 mm Hg; 2.7 kPa)

Sources & evidence

ORD record
ord-9f09f561d1464ec5918fe2126239a98a
Source dataset
uspto-grants-1990_11
Patent number
US04971979

Reaction notes

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