p-Octylbenzoic acid → HCID 178442635, compound

HRID 1612597Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[C:6]([C@H:8]2[CH2:13][CH2:12][C@H:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:10][CH2:9]2)[CH:5]=[CH:4][C:3]=1[OH:22].[CH2:23]([C:31]1[CH:39]=[CH:38][C:34]([C:35](O)=O)=[CH:33][CH:32]=1)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]>O>[CH2:23]([C:31]1[CH:39]=[CH:38][C:34]([C:35]2[O:22][C:3]3[CH:4]=[CH:5][C:6]([C@H:8]4[CH2:9][CH2:10][C@H:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:12][CH2:13]4)=[CH:7][C:2]=3[N:1]=2)=[CH:33][CH:32]=1)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]

Participants

Conditions

Temperature: 250 °C

Procedure

Step iii) In a 50 ml-round-bottomed flask, 10 g of polyphosphoric acid, 0.40 g (1.32 mM) of 2-amino-4-(trans-4-octylcyclohexyl)phenol and 0.31 g (1.32 mM) of 4-octylbenzoic acid were placed, followed by stirring for 4 hours at about 250 ° C. After the reaction, the reaction mixture was poured into water and an insoluble matter was recovered by filtration. The insoluble matter was added to 10% K2CO3 and sufficiently stirred, followed by recovery of a solid. The solid was washed with water and purified by silica gel column chromatography (eluent: toluene) to obtain 0.11 g of 2-(4-octylphenyl)-5-(trans-4-octylcyclohexyl)benzoxazole (yield: 16.7%). ##STR18##

Workup

customAfter the reaction
filtrationan insoluble matter was recovered by filtration
additionThe insoluble matter was added to 10% K2CO3
stirringsufficiently stirred
washThe solid was washed with water
custompurified by silica gel column chromatography (eluent: toluene)

Sources & evidence

ORD record: ord-583477a8902547c1832fec998194e0e6
Source dataset: uspto-grants-1993_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05190690

Reaction notes

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