1-Butanol → HCID 14097345, compound

HRID 568744

Reaction equation

HRID 568744 reaction equation
[CH3:1][O:2][C:3](=[O:19])[CH2:4][O:5][NH:6][C:7](=[O:18])[C:8]1[C:13]([Cl:14])=[CH:12][CH:11]=[C:10]([Cl:15])[C:9]=1[O:16][CH3:17].[CH2:20](O)[CH2:21][CH2:22]C.C1(C)C=CC=CC=1>CCCCO.CCCCO.CCCCO.CCCCO.[Ti].CO.C1(C)C=CC=CC=1>[CH2:1]([O:2][C:3](=[O:19])[CH2:4][O:5][NH:6][C:7](=[O:18])[C:8]1[C:13]([Cl:14])=[CH:12][CH:11]=[C:10]([Cl:15])[C:9]=1[O:16][CH3:17])[CH2:20][CH2:21][CH3:22]

Participants

6

Reactant 3

HCID 2631-ButanolHCID 1140TolueneHCID 14097344Methyl [(3,6-dichloro-2-methoxybenzoyl)aminooxy]acetate

Product 1

HCID 14097345HCID 14097345, compound

Reagents, catalysts & solvents 2

HCID 521701TetrabutoxytitaniumCatalystHCID 21867641Toluene methanolSolvent

Conditions

Temperature
85 °C

Procedure

To 161.8 g. of methyl[(3,6-dichloro-2-methoxybenzoyl) aminooxy]acetate was added 80 g. of n-butyl alcohol, 600 ml. of toluene, and 9.5 g. of titanium n-butoxide. The mixture was stirred and heated to 85° C. for 2 hours to drive off a methanol/toluene mixture. The heat was then maintained at 95°-100° C. to distill off n-butanol/toluene. The reaction mixture was cooled to 40° C. and 150 ml. of 1 M. HCl added. The mixture was then washed with 1 M. HCl, water, then saturated NaHCO3 solution, and then dried over MgOS4, filtered, and evaporated in vacuo to yield the title product as a white solid, m.p. 68°-71° C.

Workup

  1. temperatureThe heat was then maintained at 95°-100° C.
  2. distillationto distill off n-butanol/toluene
  3. temperatureThe reaction mixture was cooled to 40° C.
  4. additionHCl added
  5. washThe mixture was then washed with 1 M
  6. dry with materialHCl, water, then saturated NaHCO3 solution, and then dried over MgOS4
  7. filtrationfiltered
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-3782c88506c547c5ab4d0635db4253ab
Source dataset
uspto-grants-1988_03
Patent number
US04729781

Linked notes

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