Thiophenol → S-Phenyl 2-(4-methoxyphenyl)ethanethioate

HRID 1044428Notes

Reaction equation

HRID 1044428 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](Cl)=[O:11])=[CH:5][CH:4]=1.C(N(CC)CC)C.[C:20]1([SH:26])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.CCCC(C)C.C(OCC)(=O)C>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](=[O:11])[S:26][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 7969ThiophenolHCID 8471TriethylamineHCID 27346884-Methoxyphenylacetyl chlorideHCID 21882781Isohexane ethyl acetate

Product 1

HCID 15576549S-Phenyl 2-(4-methoxyphenyl)ethanethioateYield 97%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

2-(4-Methoxyphenyl)acetyl chloride (3.06 mL, 20.0 mmol) in 60 mL toluene was added to a solution of triethylamine (2.80 mL, 20.1 mmol) and thiophenol (2.04 mL, 20.0 mmol) in 40 mL toluene. Reaction monitoring was accomplished by TLC: iso-hexane/ethyl acetate 25:1, Rf=0.29. Workup yielded 4.99 g (97%) S-phenyl 2-(4-methoxyphenyl)ethanethioate 3 as crystalline yellow solid.

Workup

  1. customReaction monitoring

Sources & evidence

ORD record
ord-7328bc729cb249bb8e3306ef30421406
Source dataset
uspto-grants-2013_10
Patent number
US08563598B2

Reaction notes

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