Glutaric anhydride → 5-Oxo-5-(2-thienyl)valeric acid

HRID 978461Notes

Reaction equation

HRID 978461 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.[C:6]1(=[O:13])[O:12][C:10](=[O:11])[CH2:9][CH2:8][CH2:7]1>>[C:5]1([C:6]([CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[O:13])[S:1][CH:2]=[CH:3][CH:4]=1

Participants

3

Reactant 2

HCID 7940Glutaric anhydrideHCID 8030Thiophene

Product 1

HCID 2551555-Oxo-5-(2-thienyl)valeric acid

Conditions

Temperature
60 °C

Procedure

Thiophene (19.5 ml) and glutaric anhydride (27.5 g) were mixed and heated to 60° C. under a nitrogen atmosphere until all solid dissolved. The heat was removed and 2.4 grams of 85% orthophosphoric acid was added. The reaction mixture was then heated to 100° C. for four hours, cooled, and 46 ml of water added. The mixture was extracted with ether then the ether phase was extracted with aqueous sodium hydroxide solution (2.5N). The aqueous phase was cooled and made acidic by addition of 6N hydrochloric acid. Solid which precipitated out was collected on a filter, washed with water and dried under vacuum at 60° C. Yield 9.2 g N.M.R. (CDCl3)δ2.1 (m, 2H), 2.54 (t, 2H), 3.04 (t, 2H), 7.14 (t, 1H), 7.64 (dd, 1H), 7.74 (d, 1H).

Workup

  1. dissolutiondissolved
  2. customThe heat was removed
  3. addition2.4 grams of 85% orthophosphoric acid was added
  4. temperatureThe reaction mixture was then heated to 100° C. for four hours
  5. temperaturecooled
  6. addition46 ml of water added
  7. extractionThe mixture was extracted with ether
  8. extractionthe ether phase was extracted with aqueous sodium hydroxide solution (2.5N)
  9. temperatureThe aqueous phase was cooled
  10. additionmade acidic by addition of 6N hydrochloric acid
  11. customSolid which precipitated out
  12. customwas collected on a filter
  13. washwashed with water
  14. customdried under vacuum at 60° C

Sources & evidence

ORD record
ord-33c4d9c87d1e4f28b9d384e548012bc3
Source dataset
uspto-grants-1987_05
Patent number
US04665090

Reaction notes

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