Adipic Acid → Adipic anhydride

HRID 1940623Notes

Reaction equation

HRID 1940623 reaction equation
[C:1]([OH:10])(=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([OH:8])=O>C(OC(=O)C)(=O)C>[C:6]1(=[O:8])[O:10][C:1](=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

3

Reactant 1

HCID 196Adipic Acid

Product 1

HCID 567658Adipic anhydrideYield 84.9%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A solution of adipic acid (10.0 g, 68 mmol) in acetic anhydride (50 ml) was heated to reflux for 3 hours. An excess of acetic anhydride was then distilled off in vacuo leaving adipic anhydride (7.4 g). 2-Amino-3,4,6-trifluorothiophenol (200 mg, 1.1 mmol) was dissolved in NMP (1 ml) under a nitrogen stream. To the resultant solution was gradually added adipic anhydride (143 mg, 1.1 mmol) and the mixture was stirred at 100° C. for 6 hours. After naturally cooling, the mixture was diluted with water and extracted with ethyl acetate. The organic phase was extracted with aqueous sodium bicarbonate. The alkaline phase was acidified with 10% hydrochloric acid and re-extracted with ethyl acetate. The combined organic phases were dried and then evaporated to yield a residue, which was recrystallized from acetonitrile to give 5-(4,5,7-trifluorobenzothiazol-2-yl)pentanoic acid (81 mg, 26%).

Workup

  1. temperatureto reflux for 3 hours
  2. distillationAn excess of acetic anhydride was then distilled off in vacuo

Sources & evidence

ORD record
ord-4488404675b44115858caf4611758563
Source dataset
uspto-grants-1997_12
Patent number
US05700819

Reaction notes

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