Benzyl Chloride → Methyl(4-benzylthiophenyl)acetate

HRID 34410Notes

Reaction equation

HRID 34410 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([SH:11])=[CH:7][CH:6]=1.[CH2:13](Cl)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C([O-])([O-])=O.[K+].[K+].[OH-].[Na+]>C(O)C>[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([S:11][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 14033178Methyl 2-(4-mercaptophenyl)acetate

Product 1

HCID 54174016Methyl(4-benzylthiophenyl)acetate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl(4-mercaptophenyl)acetate (0.2 mol) is heated at reflux with benzyl chloride (25 g, 0.2 mol) and K2CO3 (25 g, 0.2 mol) in 100 mL ethanol. The product is added to aqueous NaOH, extracted with ether, and purified by silica gel chromatography to yield methyl(4-benzylthiophenyl)acetate (3). (Scheme III, Step 1.)

Workup

  1. extractionextracted with ether
  2. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-3bd374c3ce354367ba30e6cb8a4808a1
Source dataset
uspto-grants-1988_08
Patent number
US04761420

Reaction notes

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