4-Cyanophenol → 4-[(2-Methylbut-3-yn-2-yl)oxy]benzonitrile

HRID 2211225Notes

Reaction equation

[C:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)#[N:2].C1CCN2C(=NCCC2)CC1.Cl[C:22]([CH3:26])([CH3:25])[C:23]#[CH:24]>C(#N)C>[CH3:25][C:22]([O:9][C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1)([CH3:26])[C:23]#[CH:24]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 4-cyanophenol (655 g, 5.50 mol) in acetonitrile (10 L) at 0° C. under nitrogen was added cuprous chloride (495 mg, 5 mmol, 0.001 eq., 0.1 mol %). DBU (970 mL, 6.51 mol) was added slowly while maintaining the temperature at <5° C. 3-Chloro-3-methyl-1-butyne (570 mL, 5 mole) was added. After stirring for 4 hours at 0° C., the mixture was concentrated at reduced pressure and the residue was partitioned between ethyl acetate (5 L) and 1N HCl (2 L). The organic fraction was washed with 1N NaOH (2×1 L), water (1 L), and brine (1 L). After drying (magnesium sulfate), the solvent was removed at reduced pressure to afford the title compound as a yellow oil (930 g) which was used without further purification.

Workup

temperaturewhile maintaining the temperature at <5° C
concentrationthe mixture was concentrated at reduced pressure
customthe residue was partitioned between ethyl acetate (5 L) and 1N HCl (2 L)
washThe organic fraction was washed with 1N NaOH (2×1 L), water (1 L), and brine (1 L)
dry with materialAfter drying (magnesium sulfate)
customthe solvent was removed at reduced pressure

Sources & evidence

ORD record: ord-31355b9ef8a04ec48929db72cdb40389
Source dataset: uspto-grants-1995_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05463059

Reaction notes

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