Dichloromethane → HCID 20288210, compound

HRID 126883Notes

Reaction equation

HRID 126883 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][CH:7]([N:15]2[CH:19]=[N:18][CH:17]=[N:16]2)[CH:8]([OH:14])[C:9]([CH3:13])([CH3:12])[CH2:10][OH:11])=[CH:4][CH:3]=1.[C:22](Cl)(=[O:24])[CH3:23].[C:26](=[O:29])(O)[O-].[Na+].[CH2:31](Cl)Cl>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH:7]([N:15]2[CH:19]=[N:18][CH:17]=[N:16]2)[CH:8]([O:14][C:26](=[O:29])[CH3:31])[C:9]([CH3:12])([CH3:13])[CH2:10][O:11][C:22](=[O:24])[CH3:23])=[CH:20][CH:21]=1

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 20288249Triadimenol-tert-butylhydroxy

Product 1

HCID 20288210HCID 20288210, compoundYield 29%

Procedure

46 g (0.123 mol) of 1-(4-chlorophenoxy)-1-(1,2,4-triazol-1-yl)-3,3-dimethyl-butane-2,4-diol were warmed to 50° C. with 16 g (0.205 mol) of acetyl chloride for about 16 hours. Therefore, 500 ml of methylene chloride and then 1,000 ml of saturated sodium bicarbonate solution were added. The mixture was stirred at room temperature for 1 hour and the organic phase was separated off, washed twice with 500 ml of water each time, dried over sodium sulphate and concentrated by distilling off the solvent in vacuo. The oil which remained was taken up in 300 ml of acetone, and 23 g of naphthalene-1,5-disulphonic acid were added. The precipitate which formed was filtered off and taken up in 600 ml of methylene chloride and the methylene chloride mixture was neutralized with 1,000 ml of saturated sodium bicarbonate solution. The organic phase was separated off, washed twice with 500 ml of water each time and dried over sodium sulphate. Thereafter, it was concentrated by distilling off the solvent in vacuo. The oil which remained crystallized after adding 100 ml of diisopropyl ether. 14 g (29% of theory) of 1-(4-chlorophenoxy)-1-(1,2,4-triazol-1-yl)-3,3-dimethyl-2,4-diacetoxy-butane of melting point 84°-87° C. were obtained.

Workup

  1. customthe organic phase was separated off
  2. washwashed twice with 500 ml of water each time
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated
  5. distillationby distilling off the solvent in vacuo
  6. addition23 g of naphthalene-1,5-disulphonic acid were added
  7. customThe precipitate which formed
  8. filtrationwas filtered off
  9. customThe organic phase was separated off
  10. washwashed twice with 500 ml of water each time
  11. dry with materialdried over sodium sulphate
  12. concentrationThereafter, it was concentrated
  13. distillationby distilling off the solvent in vacuo
  14. customThe oil which remained crystallized
  15. additionafter adding 100 ml of diisopropyl ether

Sources & evidence

ORD record
ord-54cae318129e48258cdce627b3416bf0
Source dataset
uspto-grants-1981_03
Patent number
US04254132

Reaction notes

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