HCID 19021158, compound → HCID 19021147, compound

HRID 1108921Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[CH:5]=[CH:4][C:3]=1[OH:14].[CH2:15]([C:23]1[CH:31]=[CH:30][C:26]([C:27]([O-])=O)=[CH:25][CH:24]=1)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]>O>[CH2:15]([C:23]1[CH:31]=[CH:30][C:26]([C:27]2[O:14][C:3]3[CH:4]=[CH:5][C:6]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])=[CH:7][C:2]=3[N:1]=2)=[CH:25][CH:24]=1)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

Conditions

Temperature: 250 °C

Procedure

In a 50 ml-round-bottomed flask, 19 g of polyphosphoric acid, 0.30 g (1.55 mM) of 2-amino-4-hexylphenol and 0.37 g (1.58 mM) of 4-octylbenzoate acid were placed, followed by stirring for 3.5 hours at about 250° C. After the reaction, the reaction mixture was poured into water to precipitate a crystal. The crystal was recovered by filtration and was washed with 10% K2CO3. The crystal was dissolved in ethyl acetate and washed with water, followed by drying with anhydrous sodium sulfate and distilling-off of the solvent. The resultant residue was purified by silica gel column chromatography (eluent: toluene/hexane=1/2) to obtain 0.17 g of 2-(4-octylphenyl)-5-hexylbenzoxazole (yield: 28.0%). ##STR72##

Workup

customAfter the reaction
customto precipitate a crystal
filtrationThe crystal was recovered by filtration
washwas washed with 10% K2CO3
dissolutionThe crystal was dissolved in ethyl acetate
washwashed with water
dry with materialby drying with anhydrous sodium sulfate and distilling-off of the solvent
customThe resultant residue was purified by silica gel column chromatography (eluent: toluene/hexane=1/2)

Sources & evidence

ORD record: ord-1c13a90c51fd4f698dacd3053f121cfc
Source dataset: uspto-grants-1994_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05318720

Reaction notes

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