Methane → HCID 14770881, compound

HRID 1085507Notes

Reaction equation

HRID 1085507 reaction equation
[C:1]([OH:9])(=[S:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:10]=[C:11]([CH2:15][CH2:16][C:17]([OH:19])=[O:18])[C:12]([OH:14])=[O:13].C>CC(C)=O.CN(C)C1C=CN=CC=1>[C:1]([S:8][CH2:10][CH:11]([CH2:15][CH2:16][C:17]([OH:19])=[O:18])[C:12]([OH:14])=[O:13])(=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 297MethaneHCID 951552-Methyleneglutaric acidHCID 178526132HCID 178526132, compound

Product 1

HCID 14770881HCID 14770881, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

To a cooled solution (5° C.) of thiobenzoic acid (5.5 g, 39.8 mmol) in acetone (75 mL), was added 2-methyleneglutaric acid (5.25 g, 36.4 mmol) with stirring. To the resulting solution, 4-dimethylaminopyridine (0.5 g, 4.1 mmol) was added and the solution was stirred for 5 hours at 5° C. The temperature was slowly raised to 60° C. and refluxed for 20 hours. The resulting solution was treated with activated charcoal (1 g) and filtered. The clear solution was evaporated to a thick liquid and cold distilled water (100 ml) was added with rapid stirring. The white precipitate formed was filtered and suspended in a saturated aqueous solution of NaHCO3. After stirring for 15 minutes, the suspension was filtered and the clear filtrate extracted with three portions of EtOAc. The aqueous fraction was then acidified with 18% HCl. The white precipitate formed was collected by filtration, washed with cold distilled water, and dried at 50° C. The crude product was crystallized from aqueous ethanol to yield white shiny crystals, representing a yield of 7.71 g (75%) of the captioned product (mp 144° C.).

Workup

  1. stirringthe solution was stirred for 5 hours at 5° C
  2. temperaturerefluxed for 20 hours
  3. filtrationfiltered
  4. customThe clear solution was evaporated to a thick liquid
  5. distillationcold distilled water (100 ml)
  6. additionwas added with rapid stirring
  7. customThe white precipitate formed
  8. filtrationwas filtered
  9. stirringAfter stirring for 15 minutes
  10. filtrationthe suspension was filtered
  11. extractionthe clear filtrate extracted with three portions of EtOAc
  12. customThe white precipitate formed
  13. filtrationwas collected by filtration
  14. washwashed
  15. distillationwith cold distilled water
  16. customdried at 50° C
  17. customThe crude product was crystallized from aqueous ethanol
  18. customto yield white shiny crystals

Sources & evidence

ORD record
ord-3905befc22bd42b1be09c5444daa1a87
Source dataset
uspto-grants-1991_04
Patent number
US05010103

Reaction notes

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