m-Chloroperbenzoic acid → 2-(4-Decyloxyphenyl)-5-acetoxybenzoxazole

HRID 1108929

Reaction equation

HRID 1108929 reaction equation
ClC1C=CC=[C:4]([C:8]([O:10]O)=[O:9])C=1.C(=O)([O-])O.[K+].[CH2:17]([O:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]2[O:35][C:36]3[CH:42]=[CH:41][C:40](C(=O)C)=[CH:39][C:37]=3[N:38]=2)=[CH:30][CH:29]=1)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]>ClCCl>[CH2:17]([O:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]2[O:35][C:36]3[CH:42]=[CH:41][C:40]([O:10][C:8](=[O:9])[CH3:4])=[CH:39][C:37]=3[N:38]=2)=[CH:30][CH:29]=1)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acid2×HCID 516893Potassium Bicarbonate2×HCID 190211532-(4-Decyloxyphenyl)-5-acetylbenzoxazole

Product 1

HCID 190211572-(4-Decyloxyphenyl)-5-acetoxybenzoxazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 50 ml-round-bottomed flask, 1.50 g of (3.81 mM) of 2-(4-decyloxyphenyl)-5-acetylbenzoxazole was dissolved in 10 ml of dichloromethane, followed by successive addition of 0.66 g of (3.82 mM) of m-chloroperbenzoic acid and 0.40 g (4.00 mM) of potassium hydrogencarbonate and heat-refluxing for 7 hours and 40 minutes under stirring. After cooling to room temperature, 0.33 g (1.91 mM) of m-chloroperbenzoic acid and 0.20 g (2.00 mM) of potassium hydrogencarbonate was successively added, followed by heat-refluxing for 12 hours under stirring. After the reaction, the insoluble was filtered off and the filtrate was subjected to reduced pressure distillation to obtain a residue. The residue was purified by silica gel column chromatography (eluent: toluene/ethyl acetate=100/1) to obtain 2-(4-decyloxyphenyl)-5-acetoxybenzoxazole. Then, 0.51 g (7.73 mM) of potassium hydroxide was dissolved in 50 ml of ethanol under heating. To the solution, the above-prepared 2-(4-decyloxyphenyl)-5-acetoxybenzoxazole was added, followed by stirring for 30 minutes at about 60° C. After the reaction, ethanol in the reaction mixture was distilled off under reduced pressure. To the resultant residue, 50 ml of water was added, followed by addition of 0.7 ml of hydrochloric acid under stirring on an ice bath to precipitate a crystal. The crystal was recovered by filtration and washed with water, followed by recrystallization from methanol to obtain 0.27 g of 2-(4-decyloxyphenyl)-5-hydroxybenzoxazole (Yield: 19.3%).

Workup

  1. temperatureheat-refluxing for 7 hours and 40 minutes
  2. temperatureby heat-refluxing for 12 hours
  3. stirringunder stirring
  4. customAfter the reaction
  5. filtrationthe insoluble was filtered off
  6. distillationthe filtrate was subjected to reduced pressure distillation
  7. customto obtain a residue
  8. customThe residue was purified by silica gel column chromatography (eluent: toluene/ethyl acetate=100/1)

Sources & evidence

ORD record
ord-3c22a4daed8e490c82fd531db77dad96
Source dataset
uspto-grants-1994_06
Patent number
US05318720

Linked notes

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