Acetic Anhydride → 5-Acetyl-2,2'-bithienyl

HRID 1291578

Reaction equation

HRID 1291578 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[S:7][CH:8]=[CH:9][CH:10]=1.[C:11](OC(=O)C)(=[O:13])[CH3:12]>P(=O)(O)(O)O>[C:11]([C:5]1[S:1][C:2]([C:6]2[S:7][CH:8]=[CH:9][CH:10]=2)=[CH:3][CH:4]=1)(=[O:13])[CH3:12]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 681202,2'-Bithiophene

Product 1

HCID 6064225-Acetyl-2,2'-bithienyl

Reagents, catalysts & solvents 1

HCID 1004Phosphoric AcidCatalyst

Procedure

2.40 g of 2,2'-bithiophene was dissolved in 8 ml of acetic anhydride and refluxed under nitrogen gas atmosphere. 6 drops of phosphoric acid (85%) was added and reacted for 5 hours. The reaction mixture was poured onto 200 g of crushed ice cubes and stirred for 1 h. The solid deposited was collected and vacuum distilled, 5-acetyl-2,2'-bithiophene 1.98 g was obtained at 148° C./0.8 mm-Hg and the melting point was 112°-113° C. The residue was recrystallized from dioxane and 0.25 g of 5,5'-diacetyl-2,2'-bithiophene with melting point of 236°-9° C. was obtained.

Workup

  1. temperaturerefluxed under nitrogen gas atmosphere
  2. customreacted for 5 hours
  3. customThe solid deposited was collected
  4. distillationvacuum distilled

Sources & evidence

ORD record
ord-f83107f0ee2f4289897ebfccf84b8f3d
Source dataset
uspto-grants-1998_05
Patent number
US05753692

Linked notes

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