Water → Terbucromil

HRID 1606337Notes

Reaction equation

HRID 1606337 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:17]([CH3:20])([CH3:19])[CH3:18])[C:8]2OC(C)=[CH:11][C:10](=[O:15])[C:9]=2[CH:16]=1)([CH3:4])([CH3:3])[CH3:2].[Se](=O)=[O:22].[OH2:24].[O:25]1[CH2:30][CH2:29]OCC1>C(Cl)(Cl)Cl>[C:1]([C:5]1[CH:6]=[C:7]([C:17]([CH3:18])([CH3:19])[CH3:20])[C:8]2[O:24][C:29]([C:30]([OH:25])=[O:22])=[CH:11][C:10](=[O:15])[C:9]=2[CH:16]=1)([CH3:2])([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 24007Selenium DioxideHCID 312751,4-DioxaneHCID 21546409HCID 21546409, compound

Product 1

HCID 71716Terbucromil

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 2.72 parts of 6,8-di-t-butyl-2-methyl-4-oxo-4H-1-benzopyran and 4.44 parts of selenium dioxide in a mixture of 60 parts of water and 250 parts by volume of dioxan was heated under gentle reflux for 12 hours. After cooling, the solution was filtered and the solvents were evaporated from the filtrate. The residue thus produced was dissolved in 250 parts by volume of chloroform and the resulting solution was extracted with 3 portions of 100 parts of a solution containing 5 parts of sodium bicarbonate in 100 parts of water. The combined aqueous washings were acidified with concentrated hydrochloric acid to give a solid which was crystallised from aqueous ethanol to give 6,8-di-t-butyl-4-oxo-4H-1-benzopyran-2-carboxylic acid, m.p. 230°-232° C.

Workup

  1. temperaturewas heated
  2. temperatureunder gentle reflux for 12 hours
  3. temperatureAfter cooling
  4. filtrationthe solution was filtered
  5. customthe solvents were evaporated from the filtrate
  6. customThe residue thus produced
  7. extractionthe resulting solution was extracted with 3 portions of 100 parts of a solution
  8. additioncontaining 5 parts of sodium bicarbonate in 100 parts of water
  9. customto give a solid which
  10. customwas crystallised from aqueous ethanol

Sources & evidence

ORD record
ord-af42fa72f746454abb83da6b7153d2fc
Source dataset
uspto-grants-1976_04
Patent number
US03952104

Reaction notes

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