Potassium Iodide → 4'-(6-Hydroxyhexyloxy)-4-cyanobiphenyl

HRID 890902Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.Cl[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][OH:23].C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>CN(C)C=O>[OH:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

4-Hydroxy-4′-cyanobiphenyl (10.35 g, 53.0 mmol), 6-chloro-1-hexanol (9.05 g, 66.3 mmol), cesium carbonate (18.99 g, 58.3 mmol), and potassium iodide (0.88 g, 5.3 mmol) were dissolved in N,N-dimethylformamide (DMF, 130 mL). The reaction mixture was stirred at 80° C. for 6 h. The resultant salt was removed by hot filtration. The filtrate was slowly added to 600 mL water, and the crude product was collected for recrystallization from methanol to yield 8 (14.24 g, 91.0%). 1H NMR spectral data (400 MHz, CDCl3): δ 1.40-1.70 (m, 6H, CH2—), δ 1.87 (m, 2H, —CH2—), δ 3.69 (t, 2H, —CH2OAr), δ 4.03 (t, 2H, HOCH2—), δ 6.80–7.90 (m, 8H, aromatic rings).

Workup

customThe resultant salt was removed by hot filtration
additionThe filtrate was slowly added to 600 mL water
customthe crude product was collected for recrystallization from methanol

Sources & evidence

ORD record: ord-2294444066884ef38204b46ca1a919ba
Source dataset: uspto-grants-2006_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07001648B2

Reaction notes

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