1,2,3-Trimethoxybenzene → HCID 20368063, compound

HRID 616585Notes

Reaction equation

HRID 616585 reaction equation
Br[CH2:2][C:3]1[CH:4]=[N:5][O:6][CH:7]=1.[CH3:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[C:11]=1[O:18][CH3:19].C(=O)(O)[O-].[Na+]>[Cl-].[Zn+2].[Cl-].CCOCC>[CH3:17][O:16][C:12]1[CH:13]=[C:14]([CH:15]=[C:10]([O:9][CH3:8])[C:11]=1[O:18][CH3:19])[CH2:2][C:3]1[CH:4]=[N:5][O:6][CH:7]=1.[CH3:17][O:16][C:12]1[C:11]([O:18][CH3:19])=[C:10]([O:9][CH3:8])[CH:15]=[CH:14][C:13]=1[CH2:2][C:3]1[CH:4]=[N:5][O:6][CH:7]=1

Participants

7

Reactant 3

HCID 124621,2,3-TrimethoxybenzeneHCID 516892Sodium BicarbonateHCID 120182754-(bromomethyl)-1,2-oxazole2×

Product 2

HCID 20368063HCID 20368063, compoundHCID 20368065HCID 20368065, compound

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 1.0 g. of 4-bromomethyl-isoxazole, 0.816 g. of zinc chloride and 4 g. of 1,2,3-trimethoxybenzene was heated with stirring at 60° for 3 hours. At the end of this period, thin layer chromatography analysis showed the absence of starting 4-bromomethylisoxazole. The reaction was allowed to cool, diluted with 20 ml. of ether and made basic with a 5% solution of aqueous sodium bicarbonate. The aqueous layer was separated, extracted with 3 × 100 ml. of ether, and the ether extracts combined with the organic layer and dried (sodium sulfate). The solvent was removed under reduced pressure, and the desired products, 4-(3,4,5-trimethoxybenzyl)-isoxazole and 4-(2,3,4-trimethoxybenzyl)-isoxazole were isolated.

Workup

  1. additionA mixture of 1.0 g
  2. temperatureto cool
  3. additiondiluted with 20 ml
  4. customThe aqueous layer was separated
  5. extractionextracted with 3 × 100 ml
  6. dry with materialdried (sodium sulfate)
  7. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-24eb3bb58a8841a8b19ee0a6cf3bfeed
Source dataset
uspto-grants-1978_02
Patent number
US04075209

Reaction notes

Loading…