Sodium Hydroxide → 2-(4-Decyloxyphenyl)-5-carboxybenzooxazole

HRID 5280

Reaction equation

HRID 5280 reaction equation
[OH-].[Na+].Br(O)(=O)=O.Br[O-].[Na+].[CH2:10]([O:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[O:28][C:29]3[CH:35]=[CH:34][C:33]([C:36](=[O:38])C)=[CH:32][C:30]=3[N:31]=2)=[CH:23][CH:22]=1)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].Cl(O)(=O)=[O:40]>O.O1CCOCC1>[CH2:10]([O:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[O:28][C:29]3[CH:35]=[CH:34][C:33]([C:36]([OH:40])=[O:38])=[CH:32][C:30]=3[N:31]=2)=[CH:23][CH:22]=1)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

8

Reactant 5

HCID 14798Sodium HydroxideHCID 19654Chloric acidHCID 24445Bromic acidHCID 190211532-(4-Decyloxyphenyl)-5-acetylbenzoxazoleHCID 23673712Sodium hypobromite2×

Product 1

HCID 197954092-(4-Decyloxyphenyl)-5-carboxybenzooxazoleYield 75%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
-6.25 °C

Procedure

Example Compound I-51 was synthesized through the following steps: ##STR88## 1.61 g (40.3 m mole) of sodium hydroxide was dissolved in 10.7 ml of water, followed by cooling at -7.5--5° C. on ice-common salt bath. To the solution, 0.66 ml (25.6 m mole) of bromic acid was added dropwise under stirring, followed by cooling at ca. -5° C. To the mixture solution, 4.2 ml of dioxane was added dropwise under stirring to prepare sodium hypobromite solution. In a 200 ml three-neck flask, 1.50 g (3.81 m mole) of (4-decyloxyphenyl)-5-acetylbenzooxazole synthesized in Example 3, 30 ml of dioxane and 2.5 ml of water were placed, followed by keeping inner temperature below 5° C. under cooling with ice and stirring. To the mixture solution, the above-mentioned sodium hypobromite solution was added dropwise, and the reaction temperature was raised up to 45° C. and maintained for 90 minutes. After the reaction, the reaction mixture was poured into 150 ml of water. To the resultant reaction mixture, 3.2 ml of chloric acid was added to show pH=1 to precipitate a crystal. The crystal was filtered and washed with water, followed by recrystallizing from a mixture solvent of acetone-methanol to obtain 1.13 g of 2-(4-decyloxyphenyl)-5-carboxybenzooxazole (Yield: 75.0%).

Workup

  1. temperatureby cooling at ca. -5° C
  2. stirringunder stirring
  3. customtemperature below 5° C.
  4. temperatureunder cooling with ice
  5. stirringstirring
  6. temperaturethe reaction temperature was raised up to 45° C.
  7. temperaturemaintained for 90 minutes
  8. customAfter the reaction
  9. additionwas added
  10. customto precipitate a crystal
  11. filtrationThe crystal was filtered
  12. washwashed with water
  13. customby recrystallizing from a mixture solvent of acetone-methanol

Sources & evidence

ORD record
ord-07d0a3d4d786447dba463b8c0927c013
Source dataset
uspto-grants-1993_09
Patent number
US05244596

Linked notes

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