Thiophenol → Hexanethioic acid, S-phenyl ester

HRID 1184679Notes

Reaction equation

HRID 1184679 reaction equation
[C:1](Cl)(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C(N(CC)CC)C.[C:16]1([SH:22])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.CCCC(C)C.C(OCC)(=O)C>C1(C)C=CC=CC=1>[C:1](=[O:7])([S:22][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 4

HCID 7969ThiophenolHCID 8471TriethylamineHCID 67340Hexanoyl chlorideHCID 21882781Isohexane ethyl acetate

Product 1

HCID 11195139Hexanethioic acid, S-phenyl esterYield 95%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Hexanoyl chloride (2.76 mL, 19.7 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 100:1, Rf=0.20. Workup yielded 3.89 g (95%) S-phenyl hexanethioate 4 as pale yellow oil.

Workup

  1. customReaction monitoring

Sources & evidence

ORD record
ord-69c335952ace465c8da21d994674d5c6
Source dataset
uspto-grants-2014_03
Patent number
US08669283B2

Reaction notes

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