Acetyl chloride → 2-Acetylthiophene

HRID 2049126Notes

Reaction equation

HRID 2049126 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.[C:6](Cl)(=[O:8])[CH3:7].C(OC(=O)C)(=[O:12])C>CC(C)=O>[C:6]([C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)(=[O:8])[CH3:7].[S:1]1(=[O:12])[CH:5]=[CH:4][CH:3]=[CH:2]1

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 7918Acetic AnhydrideHCID 8030Thiophene

Product 2

HCID 69202-AcetylthiopheneHCID 9548690thiophene oxide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Acetylation of thiophene by acetyl chloride or acetic anhydride in the presence of various catalysts (U.S. Pat. No. 2,458,514) to obtain acetylthiophene or aceto-2 thienone or thienyl-2 methylketone and conversion of this methylketone into thienyl-2 acetamide or thienyl-2 thioacetamide by a WILLGERODT reaction, then hydrolysis of the amide (German Pat. No. 832 755).

Sources & evidence

ORD record
ord-7bc13d07a2b84d12ac5a77e02c602428
Source dataset
uspto-grants-1980_04
Patent number
US04196299

Reaction notes

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