1-Iodo-3-methylbutane → HCID 21402622, compound

HRID 1606322Notes

Reaction equation

HRID 1606322 reaction equation
[OH:1][C:2]1[C:7]2[C:8](=[O:17])[CH:9]=[C:10]([C:12]([O:14]CC)=[O:13])[O:11][C:6]=2[CH:5]=[CH:4][CH:3]=1.[Tl].I[CH2:20][CH2:21][CH:22]([CH3:24])[CH3:23]>C(Cl)(Cl)Cl>[CH3:23][CH:22]([CH3:24])[CH2:21][CH2:20][O:1][C:2]1[C:7]2[C:8](=[O:17])[CH:9]=[C:10]([C:12]([OH:14])=[O:13])[O:11][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 109241-Iodo-3-methylbutaneHCID 2801504ethyl 5-hydroxy-4-oxo-4H-chromene-2-carboxylateHCID 5359464Thallium

Product 1

HCID 21402622HCID 21402622, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
100 °C

Procedure

A stirred mixture of 21.87 parts of ethyl 5-hydroxy-4-oxo-4H-1-benzopyran-2-carboxylate, thallium salt and 99 parts of 1-iodo-3-methylbutane was refluxed for one hour. After cooling, chloroform was added to the reaction mixture and the insoluble thallium salts were removed by filtration. The chloroform filtrate was washed with cold N sodium hydroxide solution, then washed with water and the volatile components were removed by evaporation. Sodium bicarbonate solution was added to the oily residue obtained and the mixture was stirred at 100°C for two hours. After cooling, the solution was extracted with chloroform and the aqueous layer was separated. This aqueous extract was acidified with 2N hydrochloric acid and the solid which precipitated was collected by filtration, washed with water and dried to give 6.16 parts of 5-(3-methyl-n-butoxy)-4-oxo-4H-1-benzopyran-2-carboxylic acid, m.p. 181°-183°C (after crystallisation from ethyl acetate/light petroleum).

Workup

  1. temperaturewas refluxed for one hour
  2. temperatureAfter cooling
  3. customthe insoluble thallium salts were removed by filtration
  4. washThe chloroform filtrate was washed with cold N sodium hydroxide solution
  5. washwashed with water
  6. customthe volatile components were removed by evaporation
  7. additionSodium bicarbonate solution was added to the oily residue
  8. customobtained
  9. temperatureAfter cooling
  10. extractionthe solution was extracted with chloroform
  11. customthe aqueous layer was separated
  12. extractionThis aqueous extract
  13. customthe solid which precipitated
  14. filtrationwas collected by filtration
  15. washwashed with water
  16. customdried
  17. customto give
  18. custom6.16 parts of 5-(3-methyl-n-butoxy)-4-oxo-4H-1-benzopyran-2-carboxylic acid, m.p. 181°-183°C (after crystallisation from ethyl acetate/light petroleum)

Sources & evidence

ORD record
ord-9963269f940f4ce69be2fd0a5a37d785
Source dataset
uspto-grants-1976_04
Patent number
US03952104

Reaction notes

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