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

HRID 973267Notes

Reaction equation

HRID 973267 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 21.67 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. Sodiumbicarbonte soluton was added to the oily residue obtained and the mixture was stirred at 100° C for 2 hours. After cooling, the solution ws extracted with chloroform and the aqueous layer was separated. This aqueous extract was acidified with 2H 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 crystallistion 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. additionSodiumbicarbonte soluton was added to the oily residue
  8. customobtained
  9. temperatureAfter cooling
  10. extractionthe solution ws 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

Sources & evidence

ORD record
ord-a692ffbb1cbd455a95eb28441e465954
Source dataset
uspto-grants-1977_10
Patent number
US04055654

Reaction notes

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