4-Aminophenol → 4-(4-Aminophenoxy)-4'-phenylethynylbenzophenone

HRID 1450012Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[C:9]1([C:15]#[C:16][C:17]2[CH:31]=[CH:30][C:20]([C:21]([C:23]3[CH:28]=[CH:27][C:26](F)=[CH:25][CH:24]=3)=[O:22])=[CH:19][CH:18]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1>O.CC(N(C)C)=O>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:26]2[CH:27]=[CH:28][C:23]([C:21]([C:20]3[CH:30]=[CH:31][C:17]([C:16]#[C:15][C:9]4[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=4)=[CH:18][CH:19]=3)=[O:22])=[CH:24][CH:25]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 150 °C

Procedure

In a 250 mL flask equipped with nitrogen inlet, overhead stirring assembly, Dean-Stark trap, and reflux condenser were placed 4-aminophenol (5.46 g, 0.05 mol), 4-phenylethynyl-4'-fluorobenzophenone (15.02 g, 0.05 mol), potassium carbonate (7.6 g, 0.055 mol), toluene (20 mL), and DMAc (45 mL). The mixture was heated to 150° C. for 2 h, then cooled to room temperature. The reaction mixture was poured into water and the resulting light yellow powder was collected by filtration. Recrystallization from toluene afforded the desired product in 85% yield: m.p. 151°-153° C. IR (KBr); 3382 and 3314 cm-1 (NH2); 3049, 1599, and 1509 cm-1 (aromatic C--H); 2217 cm-1 (C≡C); and 1645 cm-1 (C=O): Mass Spec. m/e (relative intensity): M+, 389.4 (100); FW=389.44 g/mol.

Workup

customIn a 250 mL flask equipped with nitrogen inlet
temperatureDean-Stark trap, and reflux condenser
temperaturecooled to room temperature
filtrationthe resulting light yellow powder was collected by filtration
customRecrystallization from toluene

Sources & evidence

ORD record: ord-c9d3ff532c3a426aac71f9b92bc0b5ed
Source dataset: uspto-grants-1997_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05599993

Reaction notes

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